Isoxazole(isothiazole)-5-carboxamides

ABSTRACT

Isoxazole(isothiazole)-5-carboxamides, having herbicidal activity, of the formula ##STR1## where X is oxygen or sulfur, 
     R 1  is hydrogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted cycloalkyl, a 5- or 6-membered heterocyclic radical having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, and which may be substituted, or substituted or unsubstituted phenyl, or 
     R 2  is formyl, 4,5-dihydrooxazol-2-yl or a radical of the formula COYR 5  or CONR 6  R 7 .

This is a division of application Ser. No. 07/337,640, filed on Apr. 13,1989 now U.S. Pat. No. 5,080,708.

The present invention relates to substituted isoxazole- andisothiazole-5-carboxamides and their use for controlling undesirableplant growth.

Isoxazole- and isothiazolecarboxylic acids and their derivatives areknown. These are 5-aminocarbonyl-3-methylisoxazole-4-carboxylic acid,ethyl 5-aminocarbonyl-3-methylisoxazole-4-carboxylate,isothiazole-4,5-dicarboxamide and 5-carbamoylisothiazole-4-carboxylicacid (J. Chem. Soc. Perkin Trans. I 1982, 2391; J. Heterocycl. Chem. 22(1985), 1561 and J. Chem. Soc. 1959, 3961). Possible uses of thesesubstances are not described.

We have found that isoxazole(isothiazole)-5-carboxamides of the formulaIa ##STR2## where X is oxygen or sulfur,

R¹ is hydrogen,

C₁ -C₁₀ -alkyl which is unsubstituted or substituted by C₁ -C₃ -alkoxy,C₁ -C₃ -haloalkoxy, halogen, cyano or phenyl which may be substituted byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio. C₁ -C₄ -haloalkylthio, cyano or nitro,C₁ -C₄ -alkoxy,

C₃ -C₈ -cycloalkyl which is unsubstituted or substituted by C₁ -C₄-alkyl or halogen,

a 5-membered or 6-membered heterocyclic radical having one or twoheteroatoms selected from the group consisting of oxygen, sulfur andnitrogen, which may be substituted by C₁ -C₄ -alkyl, carboxyl or C₁ -C₄-alkoxycarbonyl,

or phenyl which is unsubstituted or substituted by C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁-C₆ -haloalkylthio, halogen, nitro or cyano,

R² is formyl, 4,5-dihydrooxazol-2-yl or a radical of the formula COYR⁵or CONR⁶ R⁷, where

Y is oxygen or sulfur,

R⁵ is hydrogen,

C₁ -C₈ -alkyl which may be substituted by C₁ -C₄ -alkoxy, C₁ -C₄-alkoxy-C₁ -C₄ -alkoxy, halogen, cyano, hydroxyl, trimethylsilyl, C₁ -C₄-alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄-alkylsulfinyl, C₁ -C₄ -alkylsulfonyl, carboxyl, C₁ -C₄ -alkoxycarbonyl,C₁ -C₄ -dialkylaminocarbonyl, C₁ -C₄ -dialkoxyphosphonyl, alkyliminooxy,benzyloxy, benzoyl which is unsubstituted or substituted by C₁ -C₄-alkyl, C₁ -C₃ -alkoxy or halogen, or phenyl which is unsubstituted orsubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl,halogen, nitro or cyano, or may be substituted by thienyl, furyl,tetrahydrofuryl, phthalimido or pyridyl,

C₃ -C₈ -alkenyl which is unsubstituted or substituted by phenyl whichmay be substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl,halogen, nitro or cyano, C₃ -C₆ -haloalkenyl,

C₃ -C₈ -alkynyl which is unsubstituted or substituted by hydroxyl or C₁-C₄ -alkoxy, C₃ -C₆ -cycloalkyl, C₅ - or C₆ -cycloalkenyl,

phenyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkyl, halogen, nitro, cyano, C₁ -C₄-alkoxycarbonyl or acylamino,

a 5-membered or 6-membered heterocyclic radical having one or twoheteroatoms selected from the group consisting of oxygen, sulfur andnitrogen or a benzotriazole radical,

C₆ - C₇ -cycloalkylimino, phthalimido, succinimido, or a radical##STR3## --CH₂ --CH(OH)--CH₂ (OH) or one equivalent of a cation from thegroup consisting of the alkali metals, alkaline earth metals, manganese,copper, iron, ammonium and substituted ammonium, or a radical ##STR4##where R⁸ and R⁹ independently of one another are each C₁ -C₄ -alkyl, C₂-C₆ -alkoxyalkyl, C₃ -C₈ -cycloalkyl, phenyl or furyl or together form amethylene chain of the formula --(CH₂)_(m) --, where m is from 4 to 7,and R⁹ is additionally hydrogen,

R⁶ is hydrogen, C₁ -C₈ -alkyl or C₃ -C₈ -cycloalkyl and R⁷ is hydrogenor C₁ -C₈ -alkyl, or

R⁶ and R⁷ form a methylene chain having 4 or 5 members, R³ is hydrogen,

C₁ -C₆ -alkyl which is unsubstituted or substituted by hydroxyl,halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -dialkylamino

or C₃ -C₈ -cycloalkyl which is unsubstituted or substituted by C₁ -C₄-alkyl, halogen or C₁ -C₄ -haloalkyl, and

R⁴ is hydrogen, hydroxyl, C₁ -C₄ -Alkoxy, C₁ -C₁₀ -alkyl which isunsubstituted or substituted by C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁-C₄ -alkylthio, C₁ -C₄ -dialkylamino, halogen, C₃ -C₆ -cycloalkyl orphenyl which may be substituted by halogen, cyano, nitro, C₁ -C₄ -alkyl,C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthioor C₁ -C₄ -halo-alkylthio, C₃ -C₁₀ -alkynyl or

C₃ -C₁₀ -alkenyl which is unsubstituted or substituted by halogen or C₁-C₄ -alkoxy,

C₃ -C₈ -cycloalkyl which is unsubstituted or substituted by C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆-haloalkylthio, halogen, nitro or cyano, C₁ -C₄ -dialkylamino, a3-membered or 6-membered heterocyclic radical which is unsubstituted orsubstituted by C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl or halogen and has oneor two heteroatoms selected from the group consisting of oxygen, sulfurand unsubstituted or methylsubstituted nitrogen, naphthyl, or phenylwhich is unsubstituted or substituted by C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁-C₆ -haloalkylthio, halogen, nitro, cyano, formyl, C₁ -C₆ -alkanoyl orC₁ -C₆ -haloalkanoyl, or R³ and R⁴ together form a radical of thestructure --(CH₂)_(n) --Y_(p) --(CH₂)₁ --, where n and q are each 1, 2or 3, p is 0 or 1 and Y is oxygen, sulfur or N-methyl, or the radical ofthe formula

    --(CH.sub.2).sub.3 --CO--

and their agriculturally acceptable salts possess herbicidal activity.

The methyl, alkoxy, alkenyl and alkynyl radicals R¹, R³, R⁴, R⁵, R⁶ andR⁷ may be straight-chain or branched and are preferably of 1 to 4 carbonatoms. The same applies to the alkyl radicals which may be present assubstituents in the radicals R¹, R³, R⁴, R⁵, R⁶ and R⁷, and to the alkylgroups in the haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio,dialkylamino, alkanoyl, haloalkanoyl and alkoxycarbonyl radicals.

Preferred halogen substituents are chlorine substituents.

The heterocyclic radicals R¹ are saturated or unsaturated. Suitableexamples are tetrahydropyranyl, tetrahydrofuryl, pyrazolyl, thienyl,furyl, pyridyl and tetrahydrofuryl. These radicals may be substituted byC₁ -C₄ -alkyl, carboxyl or C₁ -C₄ -alkylcarbonyl.

The heterocyclic radicals R⁵ may be saturated or unsaturated. Suitableradicals are thienyl, furyl, tetrahydrofuryl, triazolyl, imidazolyl,tetrahydropyranyl, pyridyl, morpholino and piperidino.

Saturated or unsaturated heterocyclic radicals R⁴ are, for example,tetrahydropyranyl, tetrahydrofuryl thiazolyl, pyridyl, morpholino,piperidino and pyrimidyl.

The novel compounds I can form addition salts, for example withinorganic and organic acids or with alkyl halides, or, if one of thesubstituents has acidic properties, they can be reacted with inorganicand organic bases to give salts. The present invention also relates tosuch salts, to the extent that they are agriculturally acceptable.

Isoxazole(isothiazole)-5-carboxamides which are preferred herbicidalactive ingredients are those of the formula Ia, where R³ is hydrogen.

Other compounds of the formula Ia which are preferred active ingredientsate those in which X is oxygen or sulfur, R¹ is hydrogen or C₁ -C₄-alkyl, R² is COYR⁵, R³ is hydrogen and R⁴ is C₁ -C₄ -alkyl or C₃ -C₈-cycloalkyl. In these compounds, R⁵ is preferably hydrogen, C₁ -C₄-alkyl, or phenyl which is unsubstituted or substituted by C₁ -C₄-alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen,or a radical ##STR5## wherein R⁸ and R⁹ in turn are preferably each C₁-C₄ -alkyl.

Isoxazole(isothiazole)-5-carboxamides of the formula ##STR6## where X,R¹, R², R³ and R⁴ have the meanings stated for formula Ia, with theproviso that X is sulfur when R¹ is CH₃, R² is COOH or COOC₂ H₅ and R³and R⁴ are each hydrogen, and that X is oxygen when R¹ is hydrogen, R²is COOH or CONH₂ and R³ and R⁴ are each hydrogen, are novel.

The isoxazole(isothiazole)-5-carboxamides of the formula I or Ia can beprepared by the following methods:

1. A process for the preparation of compounds of the formula Ib and Ia,where R² is COOR⁵ and R⁵ is hydrogen or C₁ -C₈ -alkyl (cf. Scheme 1), isbased on the reaction of a dialkyl isoxazole- orisothiazole-4,5-dicarboxylate II (R⁸ ═C₁ -C₈ -alkyl) with an aqueousbase and subsequent reaction with a mineral acid to give a carboxylicacid III. Particularly suitable dicarboxylates II are lower alkyl esters(R⁵ ═R⁸ ═C₁ -C₄ -alkyl), dimethyl and diethyl esters being particularlypreferred.

The reaction is carried out by treating a dialkyl dicarboxylate II witha strong base for example NaOH, KOH or Ca(OH)₂, at from about 0° to 80°C., preferably from 0° to 50° C., in an organic solvent, e.g. methanolor ethanol. In general, about one equivalent of the strong base is usedin aqueous solution. When the reaction is complete, the mixture iscooled and acidified with a strong mineral acid, for examplehydrochloric acid or sulfuric acid. The resulting carboxylic acid IIIcan be isolated in a conventional manner, for example by filtrationunder suction or by extraction with an organic solvent.

To convert the carboxylic acid III into the carbonyl halide IV, the acidIII is reacted in a conventional manner with an inorganic acid halide,such as thionyl chloride, a phosphorus trihalide or a phosphoruspentahalide, the chlorides being preferred. Advantageously, theinorganic acid halide is used in an amount of from 1 to 5, preferablyfrom 1 to 2, molar equivalents. The reaction can be carried out in theabsence of a solvent or in the presence of an inert organic solvent, forexample benzene or toluene, at from room temperature to the boilingpoint of the inorganic acid halide or of the inert organic solvent. Insome cases, the addition of a catalyst, such as dimethylformamide or4-dimethylaminopyridine, may be advantageous. When the reaction iscomplete, the acyl halide IV can be isolated in a conventional manner,for example by distilling off the excess inorganic acid halide and theorganic solvent and then distilling the acyl chloride IV underatmospheric or reduced pressure.

The carboxamides Ib are obtained from the carbonyl halides by reactionwith an amine V. For this purpose, it is advantageous if the carbonylhalide, in an inert organic solvent, such as dichloroethane, or anether, such as diethyl ether or methyl tert-butyl ether, is reacted withan amine V, likewise dissolved in an organic solvent. The amine V isadvantageously used in from 2 to 5, preferably from 2 to e, times themolar amount in order to bind the resulting hydrogen halide. Thereaction may also be carried out in the presence of an auxiliary base,such as a tertiary amine, e.g., triethylamine. In this case, from 1 to1.5 molar equivalents of amine V are sufficient. The reactiontemperature may be from 0° to 50° C., preferably from 0° to 20° C. Thereaction is generally complete after from 1 to 12 hours. The mixture canbe worked up in a conventional manner, for example by hydrolysis withwater and extraction of the product of the formula Ib with an organicsolvent and evaporation of the organic solvent. The product of theformula Ib can be purified, for example, by recrystallization ofchromatography.

The 4-alkoxycarbonylisoxazole-5-carboxamides or4-alkoxycarbonylisothiazole-5-carboxamides Ib can be converted into thefree carboxylic acids Ic by reaction with an aqueous base followed byreaction with a mineral acid. the react-tion is carried out by treatingthe ester Ib, in an or-ganic solvent, e.g. methanol or ethanol, with abase, e.g. NaOH, KOH or Ca(OH)₂, at from 0° to 80° C., preferably from0° to 50° C. In general, about 1-3, preferably 1-1.5, equivalents of thestrong base are used in aqueous solu-tion. When the reaction iscomplete, the mixture is acidified with a strong mineral acid, forexample hydro-chloric acid or sulfuric acid, while cooling. Theresulting carboxylic acids Ic can be isolated by filtration undersuction or by extraction with an organic solvent and evaporation of thisorganic solvent. The acid Ic may be further purified by recrystallizingor chromatographing them. ##STR7##

The dialkyl isoxazole- and isothiazole-4,5-dicarboxylates II required asstarting materials for this process are known from the literature (J.Org. Chem. 43 (1978), 3736; Chem. Parm. Bull. 28 (1980), 3296;Tetrahedron 30 (1974), 1365); those which are unknown can be prepared bymethods generally known from the literature.

2. A further process for the preparation of the compounds Id is based onthe reaction of an isoxazole- or isothiazole-5-carbonyl halide VI withan amine V. Preferred carbonyl halides VI are the chlorides. In thisprocedure, it is advantageous to react the carbonyl halide, in an inertorganic solvent, such as dichloromethane, or an ether, such as diethylether or methyl tert-butyl ether, with an amine V, likewise dissolved inan organic solvent. The amine V is advantageously used in from 2 to 5,preferably from 2 to 3, times the molar amount in order to bind theresulting hydrogen halide. The reaction may also be carried out in thepresence of an auxiliary base, for example a tertiary amine(triethylamine). In this case, from 1 to 1.5 molar equivalents of amineV are sufficient. The reaction temperature may be from 0° to 50° C.,preferably from 0° to 20° C. The reaction is generally complete afterfrom 1 to 12 hours. The mixture can be worked up in a conventionalmanner, for example by hydrolysis with water and extraction of theproduct VII with an organic solvent and evaporation of the organicsolvent.

The isoxazole- or isothiazolecarboxamides VII are converted into the5-aminocarbonylisoxazole-4-carboxylic acids or5-aminocarbonylisothiazole-4-carboxylic acids of the formula Id byreaction with an alkyllithium, preferably with the addition of a solventwhich is inert under the reaction conditions, such as diethyl ether ortetrahydrofuran. As a rule, the reaction is carried out under a nitrogenatmosphere at from -70° to -80° C. In this process, the alkyllithiumcompound is generally used in from 2 to 3 times the molar amount, basedon amide of the formula VII used. When the reaction is complete, themixture is treated with carbon dioxide, preferably in an inert solvent,such as diethyl ether or, for example, tetrahydrofuran, the desiredproducts of the formula Id, where R² is carboxyl, being obtained.

Using the same process, it is also possible to obtain isoxazole- andisothiazolecarboxamides of the formula Id, where R² is formyl, ifdimethylformamide is used instead of the carbon dioxide. Working up in aconventional manner gives substituted 4-formylisoxazole-5-carboxamidesor 4-formylisothiazole-5-carboxamides of the formula Id. ##STR8##

The isoxazole- and isothiazole-5-carbonyl halides VI required asstarting materials for this process are known from the literature. Thosewhich are unknown can be prepared from the corresponding carboxylicacids VIII in a conventional manner, as described above. ##STR9##

The carboxylic acids VIII required for this purpose are likewise knownto the literature (Chem. Ber. 106 (1973), 3345, J. Chem. Soc. 1959,3061, J. Chem. Soc. 1963, 2032, Adv. in Hterocyclic Chem. 14 (1972), 1);those which are unknown can be prepared by methods generally known fromthe literature, for example from the corresponding alcohols or aldehydesby oxidation or from the corresponding nitriles by hydrolysis.

3. Another process lead to compounds Ie, in which R² is COOR⁵ and R⁵ isC₁ -C₆ -alkyl which is unsubstituted or substituted by C₁ -C₄ -alkoxy,C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy, halogen, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulfinyl, C₁ -C₄ -alkylsulfonyl, C₁ -C₄ -alkoxycarbonyl orbenzyloxy or by phenyl which may be substituted by C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkyl, halogen, nitro or cyano, or R⁵ is C₃ -C₆-cycloalkyl or is C₃ -C₈ -alkenyl which is unsubstituted or substitutedby phenyl which may be substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁-C₄ -haloalkyl, halogen, nitro or cyano, or R⁵ is C₃ -C₈ -alkynyl, C₆ -or C₇ -cycloalkylimino, succinimido or a radical of the formula##STR10## by reaction of an acid Ic with a corresponding alcohol IX inthe presence of a strong mineral acid, for example hydrochloric acid orsulfuric acid, at from 0° to 100° C., preferably from 20° to 50° C. As arule, an excess of the alcohol IX is used, but it is also possible toemploy an inert solvent. ##STR11## 4. In a further process for thepreparation of the compounds of the formula Ie, an acid Ic is reactedwith an alcohol or thios IX in the presence of a dehydrating agent (e.g.dicyclohexylcarbodiimide (DCC)) at from -20° to 50° C., preferably from0° to 30° C. As a rule, the starting materials are used for the reactionin a roughly stoichiometric amount. The reaction is preferably carriedout in the presence of an inert solvent, for example tetrahydrofuran,dichloromethane or toluene. ##STR12## 5. Another process for thepreparation of the compounds Ic is based on the reaction of the alkylcarboxylate If with an alkali metal alkoxide X, such as sodium alkoxideor potassium alkoxide, with a corresponding alcohol IX in a conventionalmanner at from 20° C. to the boiling point of the selected alcohol IX.##STR13## 6. Compounds of the formula Ig, where R² is COOR⁵ and R⁵ is asalt-forming cation, for example an alkali metal, alkaline earth metal,ammonium or substituted ammonium ion, are obtained by reacting asubstituted isoxazole- or isothiazole-4-carboxylic acid Ic with oneequivalent of the salt-forming cation. If the cation in question is aninorganic cation, for example sodium, potassium or calcium, the acid Icis advantageously dissolved or suspended in water or in a lower alcoholor a mixture of these, and one equivalent of the salt-forming cation isadded. The salt-forming cation may be used, for example, int he form ofits hydroxide, carbonate or bicarbonate, preferably in the form of itshydroxide. The reaction is generally complete after a few minutes, andthe mixture can be worked up in a conventional manner, for example byprecipitation and filtration under suction or by evaporation of thesolvent. To prepare compounds Ig in which B⊕ is ammonium or organicammonium, the acid Ic is dissolved or suspended in an organic solvent,e.g. diethyl ether, tetrahydrofuran or dioxane, and the mixture istreated with one equivalent of ammonia, an amine or a tetraalkylammoniumhydroxide.

Among the amines which may e used the following should be mentioned:methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine,isobutylamine, secbutylamine, n-amylamine, isoamylamine, hexylamine,heptylamine, octylamine, nonylamine, decylamine, undecylamine,dodecylamine, tridecylamine, tetradecylamine, pentadecylamine,hexadecylamine, heptadecylamine, octadecylamine, methylethylamine,methylisopropylamine, methylhexylamine, methylnonylamine,methylpentadecylamine, methyloctadecylamine, ethylbutylamine,ethylheptylamine, ethyloctylamine, hexylheptylamine, hexloctylamine,dimethylamine, diethylamine, di-n-propylamine, diisopropylamine,di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine,dioctylamine, trimethylamine, triethylamine, tri-n-propylamine,triisopropylamine, tri-n-butylamine, triisobutylamine,tri-sec-butylamine, tri-n-amylamine, ethanolamine, n-propanolamine,isopropanolamine, diethyanolamine, N,N-deiethylethanolamine,N-ethylpropanolamine, N-butylethanolamine, allylamine,n-buten-2-ylamine, n-penten-2-ylamine, 2,3-dimethylbuten-2-ylamine,dibuten-2-ylamine, n-hexen-2-ylamine, propylenediamine, tallowamine,cyclopentylamine, cyclohexylamine, dicyclohexylamine, peiperidine,morpholine and pyrrolidine.

In the case of tetraalkylammonium hydroxides, for example, tetramethyl-,tetraethyl- or trimethylbenzylammonium hydroxide may be used. As a rule,the ammonium salt or organic ammonium salt is precipitated from thesolution and can be isolated by a conventional method. Alternatively,the salt of the formula Ig can also be obtained by evaporating thesolvent. ##STR14## 7. Another process leads to compounds Ih in which R²is CONR⁶ R⁷. It consists in reacting an ester Ib with a primary orsecondary amine XI. The process is carried out by reacting an ester Ibwith from 1 to 50 times the molar amount of amine XI, in the presence orabsence of an organic solvent, at from room temperature to the boilingpoint of the amine or of the organic solvent. Preferred esters Ib arelower alkyl esters, particularly the methyl and ethyl esters. Thereaction products Ih can be isolated in a conventional manner, forexample by filtration under suction or evaporation of the solution and,if required, can be further purified by recrystallization orchromatography. ##STR15## 8. In another process for the synthesis of thecompounds Ib, a dialkyl isoxazole- or isothiazole-4,5-dicarboxylate IIis reacted with an amine V.

Particularly suitable dialkyl esters II are lower alkyl esters,preferably dimethyl esters or diethyl esters. The reaction is carriedout by treating a dialkyl dicarboxylate II with about one equivalent ofa primary or secondary amine V at from 0° to 100° C., preferably from50° to 80° C., in an organic solvent, for example an alcohol, such asmethanol or ethanol. When the reaction is complete, the mixture iscooled and filtered under suction or evaporated down. The resultingproduct of the formula Ib can be further purified by a conventionalstandard method, such as recrystallization or chromatography. ##STR16##9. Compounds of the formula Ii can be obtained by reacting a substitutedisothiazole-4,5-dicarboxylic anhydride XII with an amine V. The reactionis advantageously carried out by initially taking the anhydride XII inan inert solvent, such as an ether or a halohydrocarbon, and addingdropwise about a molar amount of an amine V, if necessary likewisedissolved in an inert solvent. After the reaction is complete thereaction product is filtered off under suction or isolated byevaporating the solvent used. In some cases, the isomeric amides XIIImay be formed in this process, the amides Ii generally being thepreferred ones. ##STR17##

The isothiazole-4,5-dicarboxylic anhydrides XII required as startingmaterials for this process are known from the literature (J. Chem. Soc.1959, 3061); those which are unknown can be synthesized by methods whichare generally known from the literature.

10. In another process for the preparation of compounds of the formulaIk, an acid Ic is reacted with an alcohol or thiol XIV in the presenceof a 1-methyl-2-halopyridinium iodide at from 20° to 80° C., preferablyfrom 30° to 40° C. The reaction is carried out in the presence of aninert solvent, e.g. dichloromethane or toluene. The process is known inprinciple from the literature (Chem. Lett. 1045 (1975); ibid. 13 (1976);ibid. 49 (1976)). ##STR18##

The examples which follow illustrate the preparation of theintermediates for the synthesis of the compounds I or Ia.

EXAMPLE A

11.7 g of aniline are added dropwise to 10.0 g of3-ethylisoxazole-5-carbonyl chloride in 150 ml of dichloromethane, whilecooling with ice. The mixture is stirred overnight at room temperature,water and concentrated hydrochloric acid are added and the organic phaseis separated off, washed with sodium bicarbonate solution and evaporateddown to give 11.8 g of 3-ethylisoxazole-5-carboxanilide as colorlesscrystals of melting point 122°-124° C.

For example, the isoxazole-5-carboxamides VII can be synthesized in asimilar manner:

    ______________________________________                                         ##STR19##                   (VII)                                            R.sup.1      R.sup.4         mp. [°C.]                                 ______________________________________                                        H            i-C.sub.3 H.sub.7                                                H            tert-C.sub.4 H.sub.9                                                                          103-106                                          H            cyclo-C.sub.3 H.sub.5                                            H            cyclo-C.sub.6 H.sub.11                                           H            C.sub.6 H.sub.5                                                  CH.sub.3     H               167-171                                          CH.sub.3     i-C.sub.3 H.sub.7                                                                             92-93                                            CH.sub.3     tert-C.sub.4 H.sub.9                                                                          55-60                                            CH.sub.3     1-Ethylcyclohexyl                                                                             oil                                              CH.sub.3     4-Methyltetrahydro-                                                                           63-65                                                         pyran-4-yl                                                       CH.sub.3     C.sub.6 H.sub.5 145-147                                          CH.sub.3     4-ClC.sub.6 H.sub.4                                                                           216-219                                          CH.sub.3     3-CF.sub.3C.sub.6 H.sub.4                                                                     146-148                                          C.sub.2 H.sub.5                                                                            i-C.sub.3 H.sub.7                                                                             85-87                                            C.sub.2 H.sub.5                                                                            tert-C.sub.4 H.sub.9                                                                          67-70                                            C.sub.2 H.sub.5                                                                            4-ClC.sub.6 H.sub.4                                                                           170-173                                          C.sub.2 H.sub.5                                                                            3-CF.sub.3C.sub.6 H.sub.4                                                                     121-122                                          i-C.sub.3 H.sub.7                                                                          H                                                                i-C.sub.3 H.sub.7                                                                          CH.sub.3        69-73                                            i-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5 69-72                                            i-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                                                             79-80                                            i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                                             122-125                                          i-C.sub.3 H.sub.7                                                                          n-C.sub.4 H.sub.9                                                                             67-68                                            i-C.sub.3 H.sub.7                                                                          sec-C.sub.4 H.sub.9                                                                           133-135                                          i-C.sub.3 H.sub.7                                                                          i-C.sub.4 H.sub.9                                                                             85-86                                            i-C.sub.3 H.sub.7                                                                          tert-C.sub.4 H.sub.9                                                                          116-118                                          i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                             118-120                                          i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                             33-34                                            i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3                                                  65-66                                            i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 CH.sub.2 SCH.sub.3                                                          42                                               i-C.sub.3 H.sub.7                                                                          CH.sub.2 CH.sub.2 SCH.sub.3                                      i-C.sub.3 H.sub.7                                                                          CH.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                                                          34-36                                            i-C.sub.3 H.sub.7                                                                          CH.sub.2 CH.sub.2 OCH.sub.3                                                                   oil                                              i-C.sub.3 H.sub.7                                                                          CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                           oil                                              i-C.sub.3 H.sub.7                                                                          cyclo-C.sub.3 H.sub.5                                                                         88-90                                            i-C.sub.3 H.sub.7                                                                          cyclo-C.sub.6 H.sub.11                                                                        152-154                                          i-C.sub.3 H.sub.7                                                                          1-Methylcyclohexyl                                               i-C.sub.3 H.sub.7                                                                          1-Ethylcyclohexyl                                                                             50-51                                            i-C.sub. 3 H.sub.7                                                                         4-Methyltetrahydro-                                                                           94-96                                                         pyran-4-yl                                                       i-C.sub.3 H.sub.7                                                                          4-Ethyltetrahydro-                                                                            50-51                                                         pyran-4-yl                                                       i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 -cycloC.sub.6 H.sub.11                                                      83                                               i-C.sub.3 H.sub.7                                                                          CH.sub.2 CHCH.sub.2                                                                           65-66                                            i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 CHCH.sub.2                                                                   99-106                                          i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 CCH                                                                         85-86                                            i-C.sub.3 H.sub.7                                                                          CH.sub.2C.sub.6 H.sub.5                                                                       79-81                                            i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2 C.sub.6 H.sub.5                                i-C.sub.3 H.sub.7                                                                          CH.sub.2C(CH.sub.3).sub.3                                                                     87-89                                            i-C.sub.3 H.sub.7                                                                          C.sub.6 H.sub.5 106-108                                          i-C.sub.3 H.sub.7                                                                          4-ClC.sub.6 H.sub.4                                                                           176-178                                          i-C.sub.3 H.sub.7                                                                          3-CF.sub.3C.sub.6 H.sub.4                                                                     74-78                                            tert.-C.sub.4 H.sub.9                                                                      i-C.sub.3 H.sub.7                                                                             120-122                                          tert.-C.sub.4 H.sub.9                                                                      tert-C.sub.4 H.sub.9                                                                          129-133                                          tert.-C.sub.4 H.sub.9                                                                      C.sub.6 H.sub.5 121-122                                          tert.-C.sub.4 H.sub.9                                                                      4-ClC.sub.6 H.sub.4                                                                           158-161                                          tert.-C.sub.4 H.sub.9                                                                      3-CF.sub.3 C.sub.6 H.sub.4                                                                    104-108                                          cyclo-C.sub.6 H.sub.11                                                                     i-C.sub.3 H.sub.7                                                                             139-140                                          cyclo-C.sub.6 H.sub.11                                                                     tert-C.sub.4 H.sub.9                                                                          121-122                                          cyclo-C.sub.6 H.sub.11                                                                     cyclo-C.sub.3 H.sub.5                                                                         144-146                                          cyclo-C.sub.6 H.sub.11                                                                     cyclo-C.sub.6 H.sub.11                                           cyclo-C.sub.6 H.sub.11                                                                     C.sub.6 H.sub.5 180-181                                          Tetrahydropyran-3-yl                                                                       i-C.sub.3 H.sub.7                                                                             102-104                                          Tetrahydropyran-3-yl                                                                       tert-C.sub.4 H.sub.9                                                                          110-114                                          Tetrahydropyran-3-yl                                                                       cyclo-C.sub.3 H.sub.5                                                                         108-110                                          Tetrahydropyran-3-yl                                                                       cyclo-C.sub.6 H.sub.11                                           Tetrahydropyran-3-yl                                                                       C.sub.6 H.sub.5 149-151                                          C.sub.6 H.sub.5                                                                            i-C.sub.3 H.sub.7                                                C.sub.6 H.sub.5                                                                            tert-C.sub.4 H.sub.9                                             C.sub.6 H.sub.5                                                                            cyclo-C.sub.3 H.sub.5                                            C.sub.6 H.sub.5                                                                            cyclo-C.sub.6 H.sub.11                                           C.sub.6 H.sub.5                                                                            C.sub.6 H.sub.5                                                  4-ClC.sub.6 H.sub.4                                                                        i-C.sub.3 H.sub.7                                                                             166-171                                          4-ClC.sub.6 H.sub.4                                                                        tert-C.sub.4 H.sub.9                                                                          128-132                                          4-ClC.sub.6 H.sub.4                                                                        C.sub.6 H.sub.5 229-232                                          4-ClC.sub.6 H.sub.4                                                                        4-ClC.sub.6 H.sub.4                                              4-ClC.sub.6 H.sub.4                                                                        3-CF.sub.3C.sub.6 H.sub.4                                                                     163-165                                          cyclo-C.sub.3 H.sub.5                                                                      i-C.sub.3 H.sub.7                                                                             114-117                                          cyclo-C.sub.3 H.sub.5                                                                      tert-C.sub.4 H.sub. 9                                                                         106-107                                          cyclo-C.sub.3 H.sub.5                                                                      C.sub.6 H.sub.5 180-186                                          ______________________________________                                                                     mp. [°C.]/                                                             .sup.1 H.NMR                                     R.sup.1      R.sup.4         (CDCl.sub.3) [ppm]                               ______________________________________                                        i-C.sub.3 H.sub.7                                                                          cyclo-C.sub.5 H.sub.9                                                                         119-121                                          i-C.sub.3 H.sub.7                                                                          Tetrahydrofur-3-yl                                                                            75-78                                            i-C.sub.3 H.sub.7                                                                          Thiazol-2-yl    165-168                                          i-C.sub.3 H.sub.7                                                                          5-Methylthiazol2-yl                                                                           149-153                                          i-C.sub.3 H.sub.7                                                                          5-Ethylthiazol2-yl                                                                            157-163                                          i-C.sub.3 H.sub.7                                                                          5-n-Propylthiazol-yl                                                                          140-145                                          i-C.sub.3 H.sub.7                                                                          CH(CH.sub.3)CH.sub.2 CN                                                                       88-92                                            i-C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2CH.sub.2 CN                                                                  95-97                                            i-C.sub.3 H.sub.7                                                                          OC.sub.2 H.sub.5                                                                              33-35                                            i-C.sub.3 H.sub.7                                                                          Pyrid-2-yl      104-106                                          i-C.sub.3 H.sub.7                                                                          Pyrid-3-yl      150-152                                          i-C.sub.3 H.sub.7                                                                          Pyrid-4-yl      185-187                                          i-C.sub.3 H.sub.7                                                                          Pyrimid-2-yl    94-99                                            n-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                                             108-110                                          n-C.sub.3 H.sub.7                                                                          cyclo-C.sub.3 H.sub.5                                                                         104-106                                          n-C.sub.3 H.sub.7                                                                          tert-C.sub.4 H.sub.9                                                                          85-86                                            n-C.sub.3 H.sub.7                                                                          C.sub.6 H.sub.5 118-119                                          n-C.sub.3 H.sub.7                                                                          cyclo-C.sub.6 H.sub.11                                                                        136-137                                          s-C.sub.4 H.sub.9                                                                          i-C.sub. 3 H.sub.5                                                                            150-152                                          s-C.sub.4 H.sub.9                                                                          cyclo-C.sub.3 H.sub.5                                                                         107-111                                          s-C.sub.4 H.sub.9                                                                          tert-C.sub.4 H.sub.9                                                                          138-142                                          s-C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5  99-101                                          i-C.sub.3 H.sub.7                                                                          N(CH.sub.3).sub.2                                                                             131-133                                          CH.sub.3     N(CH.sub.3).sub.2                                                                             111-113                                          CH.sub.3     Morpholino      190-192                                          CH.sub.3     Piperidino      158-161                                          CH.sub.3     CH.sub.3        146-148                                          i-C.sub.3 H.sub.7                                                                          Piperidino      133-135                                          i-C.sub.3 H.sub.7                                                                          Morpholino      178-179                                          CH.sub.3     C.sub.2 H.sub.5 97-99                                            neo-C.sub.5 H.sub.11                                                                       CH.sub.3        128-130                                          neo-C.sub.5 H.sub.11                                                                       i-C.sub.3 H.sub.7                                                                             85-88                                            neo-C.sub.5 H.sub.11                                                                       cyclo-C.sub.3 H.sub.5                                                                         109-112                                          neo-C.sub.5 H.sub.11                                                                       tert-C.sub.4 H.sub.9                                                                          97-99                                            neo-C.sub.5 H.sub.11                                                                       C.sub.6 H.sub.5 137-140                                          n-C.sub.4 H.sub.9                                                                          CH.sub.3        74-76                                            n-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                                                              97-100                                          n-C.sub.4 H.sub.9                                                                          cyclo-C.sub.3 H.sub.5                                                                         82-86                                            n-C.sub.4 H.sub.9                                                                          tert-C.sub.4 H.sub.9                                                                          60-64                                            n-C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5 118-120                                          cyclo-C.sub.5 H.sub.9                                                                      tert-C.sub.4 H.sub.9                                                                          114-115                                          cyclo-C.sub. 5 H.sub.9                                                                     CH.sub.3        88-89                                            cyclo-C.sub.5 H.sub.9                                                                      cyclo-C.sub.3 H.sub.5                                                                         108-109                                          cyclo-C.sub.5 H.sub.9                                                                      C.sub.6 H.sub.5 146-148                                          n-C.sub.4 H.sub.9                                                                          OCH.sub.3       62-66                                            CH.sub.3OCH.sub.2                                                                          tert-C.sub.4 H.sub.7                                                                          50-55                                            CH.sub.3OCH.sub.2                                                                          cyclo-C.sub.3 H.sub.5                                                                         55-60                                            2-Methoxyphenyl                                                                            tert-C.sub.4 H.sub.9                                                                          119-120                                          2-Methoxyphenyl                                                                            cyclo-C.sub.3 H.sub.5                                                                         160-163                                          i-C.sub.3 H.sub.7                                                                          CH.sub.2 -cyclo-C.sub.3 H.sub.5                                                               77-80                                            n-C.sub.4 H.sub.9                                                                          CH.sub.2 -cyclo-C.sub.3 H.sub.5                                                               102-105                                          CH.sub.3 OCH(CH.sub.3)                                                                     tert-C.sub.4 H.sub.9                                                                          76-79                                            cyclo-C.sub.3 H.sub.5                                                                      cyclo-C.sub.5 H.sub.9                                                                         148-149                                          2,6-Difluorophenyl                                                                         tert-C.sub.4 H.sub.9                                                                          118-122                                          2,6-Difluorophenyl                                                                         cyclo-C.sub.3 H.sub.5                                                                         128-132                                          CH.sub.3     cyclo-C.sub.4 H.sub.7                                                                         114-115                                          i-C.sub.3 H.sub.7                                                                          cyclo-C.sub.4 H.sub.7                                                                         84-85                                            CH.sub.3 O   tert-C.sub.4 H.sub.9                                                                          65-68                                            ______________________________________                                         ##STR20##                   (VII)                                            R.sup.1     R.sup.3   R.sup.4                                                                              pm. [°C.]                                 ______________________________________                                        i-C.sub.3 H.sub.7                                                                         CH.sub.3  CH.sub.3                                                i-C.sub.3 H.sub.7                                                                         C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                      oil                                              ______________________________________                                    

EXAMPLE B

65 g of diethyl 3-methylisoxazole-4,5-dicarboxylate, dissolved in 100 mlof ethanol, are added dropwise to 18.9 g of potassium hydroxide in 100ml of water at room temperature. After 16 hours, the mixture is pouredonto 300 ml of water and extracted with ether, and the aqueous phase iaacidified with concentrated hydrochloric acid. Extracting withdichloromethane and evaporating down give3-methyl-4-ethoxycarbonylisoxazole-5-carboxylic acid as colorlesscrystals of melting point 54°-58° C.

EXAMPLE C

A solution of 14.9 g of NaOH in 120 ml of water and 150 ml of methanolis added dropwise to 85.5 g of dimethyl3-ethylisothiazole-4,5-dicarboxylate in 300 ml of methanol, whilecooling with ice. After 2 hours, the mixture is evaporated down, 1.5 lof water are added to the residue and the mixture is stirred, andextracted with ether. The aqueous phase is acidified with concentratedhydrochloric acid and extracted by shaking with dichloromethane. Theorganic phases are evaporated down to give 76.4 g of3-ethyl-4-methoxycarbonylisothiazole-5-carboxylic acid of melting point43°-45° C.

For example, the isoxazole(isothiazole)-5-carboxylic acids III can besynthesized similarly to Examples b and c.

    ______________________________________                                         ##STR21##                    (III)                                           R.sup.1         R.sup.5  X     mp. [°C.]                               ______________________________________                                        H               CH.sub.3 O                                                    H               C.sub.2 H.sub.5                                                                        O                                                    H               CH.sub.3 S                                                    H               C.sub.2 H.sub.5                                                                        S                                                    CH.sub.3        CH.sub.3 O                                                    CH.sub.3        CH.sub.3 S     75-81                                          CH.sub.3        C.sub.2 H.sub.5                                                                        S                                                    C.sub.2 H.sub.5 CH.sub.3 O                                                    C.sub.2 H.sub.5 C.sub.2 H.sub.5                                                                        O                                                    C.sub.2 H.sub.5 C.sub.2 H.sub.5                                                                        S                                                    n-C.sub.3 H.sub.7                                                                             CH.sub.3 O                                                    n-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                                                        O                                                    n-C.sub.3 H.sub.7                                                                             CH.sub.3 S                                                    n-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                                                        S                                                    i-C.sub.3 H.sub.7                                                                             CH.sub.3 O                                                    i-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                                                        O                                                    i-C.sub.3 H.sub.7                                                                             CH.sub.3 S     oil                                            i-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                                                        S                                                    s-C.sub.4 H.sub.9                                                                             CH.sub.3 O                                                    s-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                                                        O                                                    s-C.sub.4 H.sub.9                                                                             CH.sub.3 S                                                    s-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                                                        S                                                    tert-C.sub.4 H.sub.9                                                                          CH.sub.3 O                                                    tert-C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                                                        O                                                    tert-C.sub.4 H.sub.9                                                                          CH.sub.3 S                                                    tert-C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                                                        S                                                    cyclo-C.sub.3 H.sub.5                                                                         CH.sub.3 O                                                    cyclo-C.sub.3 H.sub.5                                                                         C.sub.2 H.sub.5                                                                        O                                                    cyclo-C.sub.3 H.sub.5                                                                         CH.sub.3 S                                                    cyclo-C.sub.3 H.sub.5                                                                         C.sub.2 H.sub.5                                                                        S                                                    cyclo-C.sub.6 H.sub.11                                                                        CH.sub.3 O                                                    cyclo-C.sub.6 H.sub.11                                                                        C.sub.2 H.sub.5                                                                        O                                                    cyclo-C.sub.6 H.sub.11                                                                        CH.sub.3 S                                                    cyclo-C.sub.6 H.sub.11                                                                        C.sub.2 H.sub.5                                                                        S                                                    Tetrahydropyran-                                                                              CH.sub.3 O                                                    3-yl                                                                          Tetrahydropyran-                                                                              C.sub.2 H.sub.5                                                                        O                                                    3-yl                                                                          Tetrahydropyran-                                                                              CH.sub.3 S                                                    3-yl                                                                          Tetrahydropyran-                                                                              C.sub.2 H.sub.5                                                                        S                                                    3-yl                                                                          C.sub.6 H.sub.5 CH.sub.3 O                                                    C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                        O                                                    C.sub.6 H.sub.5 CH.sub.3 S     139-141                                        C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                        S                                                    ______________________________________                                    

Preparation Examples for compounds I and Ia

EXAMPLE 1

2.9 g of isopropylamine are added dropwise to 10 g of diethyl3-methylisoxazole-4,5-dicarboxylate, dissolved in 100 ml of methanol,and the mixture is then refluxed. After 7 hours the mixture isevaporated down and the remaining oil is chromatographed over silica gel(using 9:1 toluene/acetone). Methyl5-isopropylaminocarbonyl-3-methylisoxazole-4-carboxylate is obtained ascolorless crystals of melting point 64°-66° C. (compound No. 1005).

EXAMPLE 2

2.6 g of the ester from Example 1 and 0.8 g of potassium hydroxide in 20ml of water and 20 ml of ethanol are stirred for 16 hours at roomtemperature. Thereafter, the mixture is diluted with water, acidifiedwith concentrated hydrochloric acid and extracted by shaking withdichloroaminocarbonyl-3-methylisoxazole-4-carboxylic acid as colorlesscrystals of melting point 86°-92° C. (compound No. 1004).

EXAMPLE 3

70 ml of n-butyllithium (1.6 molar solution in n-hexane) are addeddropwise, at -70° C. to 9.0 g of the anilide from Example a, dissolvedin 200 ml of absolute tetrahydrofuran. Stirring is carried out for halfan hour and the reaction mixture is poured onto 500 g of solid carbondioxide. After standing overnight, the mixture is evaporated down andthe residue is partitioned between H₂ O, sodium hydroxide solution andethyl acetate. By evaporating down the ethyl acetate phase, 2.0 g ofstarting material can be recovered. Acidification of the aqueous phasewith concentrated hydrochloric acid and filtration under suction give8.30 g of 5-anilinocarbonyl-3-ethylisoxazole-4-carboxylic acid ascolorless crystals of melting point 150°-152° C. (compound No. 1015).

EXAMPLE 4

5.0 g of 5-tert-butylaminocarbonyl-3-methylisoxazole-4-carboxylic acidare dissolved in 200 ml of methanol, and 5 ml of concentrated H₂ SO₄ areadded. After 2 days, the mixture is evaporated down, the residue ispartitioned between ethyl acetate and water and the organic phase isevaporated down. 4.0 g of methyl5-tert-butylaminocarbonyl-3-methylisoxazole-4-carboxylate are obtainedas a colorless oil (compound No. 1007). H-NMR (CDCl₃): d=1.48 (s; 9H),2.50 (s; 3H), 3.99 (s; 1H), 9.42 (bs; 1H, NH).

EXAMPLE 5 a) 3-Ethyl-4-methoxycarbonylisothiazole-5-carbonyl chloride

73 g of the carboxylic acid from Example c and 80 g of thionyl chloridein 200 ml of toluene are refluxed in the presence of a littledimethylformamide until the evolution of gas is complete. The crudecarbonyl chloride which remains in quantitative yield after evaporationis directly reacted further.

b) Methyl 5-isopropylaminocarbonyl-3-ethylisothiazole-4-carboxylate

8.4 g of isopropylamine are slowly added dropwise to 16.5 g of the crudeacyl chloride from a) in 200 ml of dichloromethane, while cooling withice. Stirring is carried out overnight, hydrolysis is effected with 150ml of water and the organic phase is separated off, washed withbicarbonate solution, dilute hydrochloric acid and water and thenevaporated down. 16.2 g of methyl5-isopropylaminocarbonyl-3-ethylthiazole-4-carboxylate of melting point55°-56° C. (compound No. 3007) are obtained.

EXAMPLE 6

2.8 g of KOH in 30 ml of water are added to 11 g of the ester fromExample 5 in 50 ml of ethanol, and the mixture is stirred overnight atroom temperature. It is diluted with 150 ml of water and extracted withether, and the aqueous phase is acidified with concentrated hydrochloricacid. Extraction by shaking with dichloromethane and evaporation give 10g of 5-isopropylaminocarbonyl-3-ethylisothiazole-4-carboxylic acid ofmelting point 138°-140° C. (compound No. 3006).

EXAMPLE 7

4.0 g of methyl 5-tert-butyaminocarbonyl-3-methylisoxazole-4-carboxylateand 50 ml of concentrated ammonia are refluxed for 3 hours. Aftercooling, the mixture is diluted with water and extracted withdichlormethane and the organic phase is evaporated down.5-tert-butylaminocarbonyl-3-methylisoxazole-4-carboxamide is obtained ascolorless crystals of melting point 155°-158° C. (compound No. 1).

EXAMPLE 8

56 ml of butyllithium (1.6 molar solution in n-hexane) are addeddropwise, at -78° C., to 8 g of the tertbutylamide of3-methylisoxazole-5-carboxylic acid in 150 ml of tetrahydrofuran. Themixture is stirred for 1 hour, after which 22 ml of dimethylformamideare slowly added dropwise. The mixture is allowed to reach roomtemperature overnight and is hydrolyzed with water, neutralized withconcentrated hydrochloric acid and extracted with ether. The oil whichremains after evaporation is chromatographed over silica gel singcyclohexane/ethyl acetate. The tert-butylamide of4-formyl-3-methylisoxazole-5-carboxylic acid is obtained as the firstfraction, in the form of pale yellow crystals of melting point 36°-38°C. (compound No. 2).

EXAMPLE 9 a) 3-Methyl-4-ethoxycarbonylixoxazole-5-carbonyl chloride

13.3 g of carboxylic acid from Example b and 20 ml of thionyl chlorideare refluxed in the presence of a little dimethylformamide until theevolution of gas is complete. The crude carbonyl chloride which remainsin quantitative yield after evaporation is directly reacted further.

b) 3.4 g of diethylamine are slowly added dropwise to 5 g of the crudeacyl chloride from a) in 100 g of dichloromethane, while cooling withice. Stirring is carried out overnight, hydrolysis is effected withwater and the organic phase is separated off, washed with bicarbonateand then evaporated down. 5.0 g of ethyl5-diethylaminocarbonyl-3-methylisoxazole-4-carboxylate are obtained as abrown oil (compound No. 3).

H-NMR (CDCl₃): δ=1.15 (t; 3H), 1.27 and 1.31 (2t; 6H), 2.50 (s; 3H),3.17 (q; 2H), 3.58 (q; 2H), 4.28 (q; 2H).

EXAMPLE 10

5.0 g of the ester from Example 9 and 1.4 g of potassium hydroxide in 10ml of water and 20 ml of ethanol are stirred at room temperature. Whenthe reaction is complete, the mixture is diluted with water andextracted with dichloromethane. Thereafter, the aqueous phase isacidified with hydrochloric acid and extracted with dichlormethane, andthe organic phase is evaporated down. 3.0 g of5-diethylaminocarbonyl-3-methylisoxazole-4-carboxylic acid are obtainedas a pale oil (compound No. 4).

H-NMR (CDCl₃ : δ=1.28 and 1.32 (2t; 6H), 2.60 (s; 3H), 3.59 and 3.62(2q; 4H), 10.50 (bs; 1H, COOH).

EXAMPLE 11

A mixture of 1.2 g of 2-methylpropane-2-thiol, 3.0 g of5-tert-butylaminocarbonyl-3-methylisoxazole-4-carboxylic acid and 5.9 gof tri-n-butylamine in 20 ml of dichloromethane is added dropwise to astirred suspension of 4.1 g of 1-methyl-2-chloropyridinium iodide in 40ml of dichloromethane at room temperature. The mixture is refluxed for 3hours, the solvent is stripped off under reduced pressure and the crudeproduct is purified by column chromatography over silica gel. 2.1 g ofthe tert-butyl thioester of5-tert-butylaminocarbonyl-3-methylisoxazole-4-carboxylic acid areobtained as a yellow oil (compound No. 2003).

For example, the compounds mentioned in Tables 1 to 3 below can beprepared similarly to Examples 1 to 10.

                                      TABLE 1                                     __________________________________________________________________________     ##STR22##                                                                                                               mp [°C.]/.sup.1 H-NMR       No.                                                                              R.sup.1     R.sup.5         R.sup.4     (CDCl.sub.3)                       __________________________________________________________________________                                               [ppm]                              1001                                                                             H           H               i-C.sub.3 H.sub.7                              1002                                                                             H           H               tert.-C.sub.4 H.sub.9                                                                     oil 1.55(s; 9H),                                                              7.50(bs; 1H,                                                                  NH), 8.78(s; 1H)                   1003                                                                             CH.sub.3    H               H           266-268                            1004                                                                             CH.sub.3    H               i-C.sub.3 H.sub.7                                                                         86-92                              1005                                                                             CH.sub.3    CH.sub.3        i-C.sub.3 H.sub.7                                                                         64-66                              1006                                                                             CH.sub.3    H               tert.-C.sub.4 H.sub.9                                                                     92-94                              1007                                                                             CH.sub.3    CH.sub.3        tert.-C.sub.4 H.sub.9                          1008                                                                             CH.sub.3    H               1-ethylcyclohexyl                                                                         119-121                            1009                                                                             CH.sub.3    H               4-methyltetrahydro-                                                                       80-87                                                             pyran-4-yl                                     1010                                                                             CH.sub.3    H               C.sub.6 H.sub.5                                                                           204-210                            1011                                                                             CH.sub.3    H               4-ClC.sub.6 H.sub.4                                                                       233-237                            1012                                                                             CH.sub.3    H               3-CF.sub.3C.sub.6 H.sub.4                                                                 188-191                            1013                                                                             C.sub.2 H.sub.5                                                                           H               i-C.sub.3 H.sub.7                                                                         63-66                              1014                                                                             C.sub.2 H.sub.5                                                                           H               tert.-C.sub.4 H.sub.9                                                                     53-58                              1015                                                                             C.sub.2 H.sub.5                                                                           H               C.sub.6 H.sub.5                                                                           150-152                            1016                                                                             C.sub.2 H.sub.5                                                                           H               4-ClC.sub.6 H.sub.4                                                                       193-196                            1017                                                                             C.sub.2 H.sub.5                                                                           h               3-CF.sub.3C.sub.6 H.sub.4                                                                 160-162                            1018                                                                             i-C.sub.3 H.sub.7                                                                         H               H                                              1019                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.3    147-148                            1020                                                                             i-C.sub.3 H.sub.7                                                                         H               C.sub.2 H.sub.5                                                                           100-101                            1021                                                                             i-C.sub.3 H.sub.7                                                                         H               n-C.sub.3 H.sub.7                                                                         85-86                              1022                                                                             i-C.sub.3 H.sub.7                                                                         H               i-C.sub.3 H.sub.7                                                                         98-99                              1023                                                                             i-C.sub.3 H.sub.7                                                                         H               n-C.sub.4 H.sub.9                                                                         96-97                              1024                                                                             i-C.sub.3 H.sub.7                                                                         H               i-C.sub.4 H.sub.9                                                                         112-114                            1025                                                                             i-C.sub.3 H.sub.7                                                                         H               sec-C.sub.4 H.sub.9                                                                       oil 1.00(t; 3H),                                                              1.32(d; 3H),                                                                  1.37(d; 6H),                                                                  1.64(quint;                                                                   2H), 3.78(sept;                                                               1H), 4.15(m;                                                                  1H), 7.00(bs;                                                                 1H, NH)                            1026                                                                             i-C.sub.3 H.sub.7                                                                         H               tert.-C.sub.4 H.sub.9                                                                     94-98                              1027                                                                             i-C.sub.3 H.sub.7                                                                         H               C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                         44-46                              1028                                                                             i-C.sub.3 H.sub.7                                                                         H               C(CH.sub.3).sub.2 C.sub.3 H.sub.7                                                         52-53                              1029                                                                             i-C.sub.3 H.sub.7                                                                         H               C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.                                   3           89-91                              1030                                                                             i-C.sub.3 H.sub.7                                                                         H               C(CH.sub.3).sub.2 CH.sub.2 SCH.sub.3                                                      oil 1.35(d; 3H),                                                              1.56(s; 6H),                                                                  2.18(s; 3H),                                                                  2.99(s; 2H),                                                                  3.77(sept; 1H),                                                               7.30(bs; 1H, NH)                   1031                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.2 CH.sub.2 SCH.sub.3                    1032                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                                                      116-118                            1033                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.2 CH.sub.2 OCH.sub.3                                                               69-71                              1034                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2            1035                                                                             i-C.sub.3 H.sub.7                                                                         H               cyclo-C.sub.3 H.sub.5                                                                     74-76                              1036                                                                             i-C.sub.3 H.sub.7                                                                         H               cyclo-C.sub.6 H.sub.11                                                                    112-114                            1037                                                                             i-C.sub.3 H.sub.7                                                                         H               1-ethylcyclohexyl                                                                         89-90                              1038                                                                             i-C.sub.3 H.sub.7                                                                         H               4-methyltetrahydro-                                                                       129-130                                                           pyran-4-yl                                     1039                                                                             i-C.sub.3 H.sub.7                                                                         H               1-C(CH.sub.3).sub.2 -cycloC.sub.6 H.sub.11                                                144-146                            1040                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.2 CHCH.sub.2                                                                       92-94                              1041                                                                             i-C.sub.3 H.sub.7                                                                         H               C(CH.sub.3).sub.2 CHCH.sub.2                                                              oil; 1.35(d; 6H),                                                             1.62(s; 6H),                                                                  3.78(sept; 1H),                                                               5.20(d; 1H),                                                                  5.25(d; 1H),                                                                  6.10(dd; 1H),                                                                 7.10(bs; 1H, NH)                   1042                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.2 C.sub.6 H.sub.5                                                                  oil 1.30(d; 6H),                                                              3.74(sept; 1H),                                                               4.70(d; 2H),                                                                  7.35(bs; 5H),                                                                 7.85(bt; 1H, NH)                   1043                                                                             i-C.sub.3 H.sub.7                                                                         H               C(CH.sub.3).sub.2 C.sub.6 H.sub.5              1044                                                                             i-C.sub.3 H.sub.7                                                                         H               CH.sub.2 C(CH.sub.3).sub.3                                                                76                                 1045                                                                             i-C.sub.3 H.sub.7                                                                         H               C.sub.6 H.sub.5                                                                           138-140                            1046                                                                             i-C.sub.3 H.sub.7                                                                         H               4-ClC.sub.6 H.sub.4                                                                       170-173                            1047                                                                             i-C.sub.3 H.sub.7                                                                         H               3-CF.sub.3C.sub.6 H.sub.4                                                                 127                                1048                                                                             tert.-C.sub.4 H.sub.9                                                                     H               i-C.sub.3 H.sub.7                                                                         84-85                              1049                                                                             tert.-C.sub.4 H.sub.9                                                                     H               tert.-C.sub.4 H.sub.9                                                                     129-133                            1050                                                                             tert.-C.sub. 4 H.sub.9                                                                    H               C.sub.6 H.sub.5                                                                           132-137                            1051                                                                             tert.-C.sub.4 H.sub.9                                                                     H               4-ClC.sub.6 H.sub.4                                                                       188-191                            1052                                                                             tert.-C.sub.4 H.sub.9                                                                     H               3-CF.sub.3C.sub.6 H.sub.4                                                                 160-162                            1053                                                                             cyclo-C.sub.6 H.sub.11                                                                    H               i-C.sub.3 H.sub.7                                                                         116-118                            1054                                                                             cyclo-C.sub.6 H.sub.11                                                                    H               tert.-C.sub.4 H.sub.9                                                                     158-159                            1055                                                                             cyclo-C.sub.6 H.sub.11                                                                    H               cyclo-C.sub.3 H.sub.5                                                                     142-143                            1056                                                                             cyclo-C.sub.6 H.sub.11                                                                    H               cyclo-C.sub.6 H.sub.11                         1057                                                                             cyclo-C.sub.6 H.sub.11                                                                    H               C.sub.6 H.sub.5                                                                           198-199                            1058                                                                             4-ClC.sub.6 H.sub.4                                                                       H               i-C.sub.3 H.sub.7                                                                         165-168                            1059                                                                             4-ClC.sub.6 H.sub.4                                                                       H               tert.-C.sub.4 H.sub.9                                                                     165-168                            1060                                                                             4-ClC.sub.6 H.sub.4                                                                       H               C.sub.6 H.sub.5                                                                           220                                1061                                                                             4-ClC.sub.6 H.sub.4                                                                       H               4-ClC.sub.6 H.sub.4                            1062                                                                             4-ClC.sub.6 H.sub.4                                                                       H               3-CF.sub.3C.sub.6 H.sub.4                                                                 209-211                            1063                                                                             i-C.sub.3 H.sub.7                                                                         succinimido     cyclo-C.sub.3 H.sub.5                                                                     108-109                            1064                                                                             CH.sub.3    H               C(CH.sub.3).sub.2 CCH                                                                     80-87                              1065                                                                             CH.sub.3    C.sub.2 H.sub.5 C(CH.sub.3).sub.2 CCH                                                                     82-86                              1066                                                                             CH.sub.3    Na.sup.⊕    tert.-C.sub.4 H.sub.9                                                                     220                                1067                                                                             CH.sub.3    K.sup.⊕     tert.-C.sub.4 H.sub.9                                                                     288                                1068                                                                             CH.sub.3    H.sub.3 N.sup.⊕ CH(CH.sub.3).sub.2                                                        tert.-C.sub.4 H.sub.9                                                                     184-187                            1069                                                                             CH.sub.3    H.sub.3 N.sup.⊕CH.sub.2 CH.sub.2 OH                                                       tert.-C.sub.4 H.sub.9                                                                     124-126                            1070                                                                             C.sub.2 H.sub.5                                                                           Na.sup.⊕    tert.-C.sub.4 H.sub.9                                                                     150                                1071                                                                             C.sub.2 H.sub.5                                                                           K.sup.⊕     tert.-C.sub.4 H.sub.9                                                                     220                                1072                                                                             C.sub.2 H.sub.5                                                                           H.sub.3 N.sup.⊕CH(CH.sub.3).sub.2                                                         tert.-C.sub.4 H.sub.9                                                                     170-172                            1073                                                                             C.sub.2 H.sub.5                                                                           H.sub.3 N.sup.⊕CH.sub.2 CH.sub.2 OH                                                       tert.-C.sub.4 H.sub.9                                                                     105-108                            1074                                                                             C.sub.2 H.sub.5                                                                           succinimido     tert.-C.sub.4 H.sub.9                                                                     163-165                            1075                                                                             C.sub.2 H.sub.5                                                                           NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     68-70                              1076                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2 CCH    tert.-C.sub.4 H.sub.9                                                                     oil 135(t; 3H),                                                               1.48(s; 9H),                                                                  2.63(t; 1H),                                                                  2.96; 4.98(d;                                                                 2H), 8.95(bs;                                                                 1H, NH)                            1077                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                            tert.-C.sub.4 H.sub.9                                                                     74-76                              1078                                                                             cyclo-C.sub.3 H.sub.5                                                                     H               i-C.sub.3 H.sub.7                                                                         78-80                              1079                                                                             cyclo-C.sub.3 H.sub.5                                                                     H               tert.-C.sub.4 H.sub.9                                                                     87-88                              1080                                                                             cyclo-C.sub.3 H.sub.5                                                                     H               C.sub.6 H.sub.5                                                                           162-163                            1081                                                                             cyclo-C.sub.6 H.sub.11                                                                    succinimido     i-C.sub.3 H.sub.7                                                                         126-127                            1082                                                                             cyclo-C.sub.6 H.sub.11                                                                    succinimido     tert.-C.sub.4 H.sub.9                                                                     172-174                            1083                                                                             cyclo-C.sub.6 H.sub.11                                                                    succinimido     C.sub.6 H.sub.5                                                                           176-177                            1084                                                                             tetrahydro- H               i-C.sub.3 H.sub.7                                                                         157-160                               pyran-3-yl                                                                 1085                                                                             tetrahydro- H               tert.-C.sub.4 H.sub.9                                                                     91-95                                 pyran-3-yl                                                                 1086                                                                             tetrahydro- H               cyclo-C.sub.3 H.sub.5                                                                     158-160                               pyran-3-yl                                                                 1087                                                                             tetrahydro- H               C.sub.6 H.sub.5                                                                           152-157                               pyran-3-yl                                                                 1088                                                                             CH.sub.3    pyrid-3-yl      tert.-C.sub.4 H.sub.9                                         methyl                                                         1089                                                                             CH.sub.3    thien-2-yl-     tert.-C.sub.4 H.sub.9                                         methyl                                                         1090                                                                             CH.sub.3    CH.sub.2CH.sub.2N(CH.sub.3).sub.2                                                             tert.-C.sub.4 H.sub.9                          1091                                                                             CH.sub.3                                                                                   ##STR23##      tert.-C.sub.4 H.sub.9                          1092                                                                             CH.sub.3    CH.sub.2CF.sub.3                                                                              tert.-C.sub.4 H.sub.9                          1093                                                                             CH.sub.3    CH.sub.2C(CH.sub.3)CH.sub.2                                                                   tert.-C.sub.4 H.sub.9                          1094                                                                             CH.sub.3    CH.sub.2 C(Cl)CH.sub.2                                                                        tert.-C.sub.4 H.sub.9                          1095                                                                             CH.sub.3    CH.sub.2CCCH.sub.2 OH                                                                         tert.-C.sub.4 H.sub.9                          1096                                                                             CH.sub.3                                                                                   ##STR24##      tert.-C.sub.4 H.sub.9                          1097                                                                             CH.sub.3                                                                                   ##STR25##      tert.-C.sub.4 H.sub.9                          1098                                                                             CH.sub.3                                                                                   ##STR26##      tert.-C.sub.4 H.sub.9                          1099                                                                             CH.sub.3    phenethyl       tert.-C.sub.4 H.sub.9                          1100                                                                             CH.sub.3    CH(C.sub.6 H.sub.5)COOCH.sub.3                                                                tert.-C.sub.4 H.sub.9                          1101                                                                             CH.sub.3    cyclo-C.sub.6 H.sub.11                                                                        tert.-C.sub.4 H.sub.9                          1102                                                                             CH.sub.3    CH.sub. 2OCH.sub.2C.sub.6 H.sub.5                                                             tert.-C.sub.4 H.sub.9                          1103                                                                             CH.sub.3    tetrahydro-     tert.-C.sub.4 H.sub.9                                         pyran-2-yl                                                     1104                                                                             CH.sub.3    tetrahydro-     tert.-C.sub.4 H.sub.9                                         fur-2-yl                                                       1105                                                                             CH.sub.3    (4-bromobenzoyl)-                                                                             tert.-C.sub.4 H.sub.9                                         methyl                                                         1106                                                                             CH.sub.3    (4-methoxybenzoyl)-                                                                           tert.-C.sub.4 H.sub.9                                         methyl                                                         1107                                                                             CH.sub.3    CH(COOCH.sub.3).sub.2                                                                         tert.-C.sub.4 H.sub.9                          1108                                                                             CH.sub.3    phthalimidomethyl                                                                             tert.-C.sub.4 H.sub.9                          1109                                                                             CH.sub.3    CH.sub.2CH.sub.2Si(CH.sub.3).sub.3                                                            tert.-C.sub.4 H.sub.9                          1110                                                                             CH.sub.3    CH.sub.2CH.sub.2ONC(CH.sub.3).sub.2                                                           tert.-C.sub.4 H.sub.9                          1111                                                                             CH.sub.3    CH.sub.2PO(OC.sub.2 H.sub.5).sub.2                                                            tert.-C.sub.4 H.sub.9                          1112                                                                             CH.sub.3    fur-2-yl-methyl tert.-C.sub.4 H.sub.9                          1113                                                                             CH.sub.3    tetrahydrofur-2-                                                                              tert.-C.sub.4 H.sub.9                                         yl-methyl                                                      1114                                                                             CH.sub.3    pyrid-2-ylmethyl                                                                              tert.-C.sub.4 H.sub.9                          1115                                                                             CH.sub.3    pyrid-4-ylmethyl                                                                              tert.-C.sub.4 H.sub.9                          1116                                                                             CH.sub.3    piperidino      tert.-C.sub.4 H.sub.9                          1117                                                                             CH.sub.3    phthalimido     tert.-C.sub.4 H.sub.9                          1118                                                                             CH.sub.3                                                                                   ##STR27##      tert.-C.sub.4 H.sub.9                          1119                                                                             CH.sub.3    NCHC.sub.6 H.sub.5                                                                            tert.-C.sub.4 H.sub.9                          1120                                                                             CH.sub.3                                                                                   ##STR28##      tert.-C.sub.4 H.sub.9                          1121                                                                             CH.sub.3    CH(CH.sub.3)CH(OCH.sub.3).sub.2                                                               tert.-C.sub.4 H.sub.9                          1122                                                                             CH.sub.3    CH.sub.2CON(C.sub.2 H.sub.5).sub.2                                                            tert.-C.sub.4 H.sub.9                          1123                                                                             CH.sub.3    N(C.sub.2 H.sub.5).sub.2                                                                      tert.-C.sub.4 H.sub.9                          1124                                                                             C.sub.2 H.sub.5                                                                           cyclo-C.sub.6 H.sub.11                                                                        tert.-C.sub.4 H.sub.9                          1125                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2OCH.sub.2C.sub.6 H.sub.5                                                              tert.-C.sub.4 H.sub.9                          1126                                                                             C.sub.2 H.sub.5                                                                           tetrahydro-     tert.-C.sub.4 H.sub.9                                         pyran-2-yl                                                     1127                                                                             C.sub.2 H.sub.5                                                                           tetrahydro-     tert.-C.sub.4 H.sub.9                                         fur-2-yl                                                       1128                                                                             C.sub.2 H.sub.5                                                                           (4-bromobenzoyl)-                                                                             tert.-C.sub.4 H.sub.9                                         methyl                                                         1129                                                                             C.sub.2 H.sub.5                                                                           (4-methoxybenzoyl)                                                                            tert.-C.sub.4 H.sub.9                                         methyl                                                         1130                                                                             C.sub.2 H.sub.5                                                                           CH(COOCH.sub.3).sub.2                                                                         tert.-C.sub.4 H.sub.9                          1131                                                                             C.sub.2 H.sub.5                                                                           phthalimidomethyl                                                                             tert.-C.sub.4 H.sub.9                          1132                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2CH.sub.2Si(CH.sub.3).sub.3                                                            tert.-C.sub.4 H.sub.9                          1133                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2CH.sub.2ONC(CH.sub.3).sub.2                                                           tert.-C.sub.4 H.sub.9                          1134                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2PO(OC.sub.2 H.sub.5).sub.2                                                            tert.-C.sub.4 H.sub.9                          1135                                                                             C.sub.2 H.sub.5                                                                           fur-2-ylmethyl  tert.-C.sub.4 H.sub.9                          1136                                                                             C.sub.2 H.sub.5                                                                           tetrahydrofur-2-                                                                              tert.-C.sub.4 H.sub.9                                         yl-methyl                                                      1137                                                                             C.sub.2 H.sub.5                                                                           pyrid-2-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                          1138                                                                             C.sub.2 H.sub.5                                                                           pyrid-4-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                          1139                                                                             C.sub.2 H.sub.5                                                                           pyrid-3-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                          1140                                                                             C.sub.2 H.sub.5                                                                           thien-2-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                          1141                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2CH.sub.2N(CH.sub.3).sub.2                                                             tert.-C.sub.4 H.sub.9                          1142                                                                             C.sub.2 H.sub.5                                                                            ##STR29##      tert.-C.sub.4 H.sub.9                          1143                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2CF.sub.3                                                                              tert.-C.sub.4 H.sub.9                          1144                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2C(CH.sub.3)CH.sub.2                                                                   tert.-C.sub.4 H.sub.9                          1145                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2 C(Cl)CH.sub.2                                                                        tert.-C.sub.4 H.sub.9                          1146                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2 C CH.sub.2 OH                                                                        tert.-C.sub.4 H.sub.9                          1147                                                                             C.sub.2 H.sub.5                                                                            ##STR30##      tert.-C.sub.4 H.sub.9                          1148                                                                             C.sub.2 H.sub.5                                                                            ##STR31##      tert.-C.sub.4 H.sub.9                          1149                                                                             C.sub.2 H.sub.5                                                                            ##STR32##      tert.-C.sub.4 H.sub.9                          1150                                                                             C.sub.2 H.sub.5                                                                           phenethyl       tert.-C.sub.4 H.sub.9                          1151                                                                             C.sub.2 H.sub.5                                                                           CH(C.sub.6 H.sub.5)COOCH.sub.3                                                                tert.-C.sub.4 H.sub.9                          1152                                                                             C.sub.2 H.sub.5                                                                           piperidino      tert.-C.sub.4 H.sub.9                          1153                                                                             C.sub.2 H.sub.5                                                                           phthalimido     tert.-C.sub.4 H.sub.9                          1054                                                                             C.sub.2 H.sub.5                                                                            ##STR33##      tert.-C.sub.4 H.sub.9                          1055                                                                             C.sub.2 H.sub.5                                                                           NCHC.sub. 6 H.sub.5                                                                           tert.-C.sub.4 H.sub.9                          1156                                                                             C.sub.2 H.sub.5                                                                            ##STR34##      tert.-C.sub.4 H.sub.9                          1157                                                                             C.sub.2 H.sub.5                                                                           CH(CH.sub.3)CH(OCH.sub.3).sub.2                                                               tert.-C.sub.4 H.sub.9                          1158                                                                             C.sub.2 H.sub.5                                                                           CH.sub.2CON(C.sub.2 H.sub.5).sub.2                                                            tert.-C.sub.4 H.sub.9                          1159                                                                             C.sub.2 H.sub.5                                                                           N(C.sub.2 H.sub.5).sub.2                                                                      tert.-C.sub.4 H.sub.9                          1160                                                                             i-C.sub.3 H.sub.7                                                                         cyclo-C.sub.6 H.sub.11                                                                        tert.-C.sub.4 H.sub.9                          1161                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2OCH.sub.2C.sub.6 H.sub.5                                                              tert.-C.sub.4 H.sub.9                          1162                                                                             i-C.sub.3 H.sub.7                                                                         tetrahydro-     tert.-C.sub.4 H.sub.9                                         pyran-2-yl                                                     1163                                                                             i-C.sub.3 H.sub.7                                                                         tetrahydro-     tert.-C.sub.4 H.sub.9                                         fur-2-yl                                                       1164                                                                             i-C.sub.3 H.sub.7                                                                         (4-bromo-benzoyl)-                                                                            tert.-C.sub.4 H.sub.9                                         methyl                                                         1165                                                                             i-C.sub.3 H.sub.7                                                                         (4-methoxybenzoyl)                                                                            tert.-C.sub.4 H.sub.9                                         methyl                                                         1166                                                                             i-C.sub.3 H.sub.7                                                                         CH(COOCH.sub.3).sub.2                                                                         tert.-C.sub.4 H.sub.9                          1167                                                                             i-C.sub.3 H.sub.7                                                                         phthalimidomethyl                                                                             tert.-C.sub.4 H.sub.9                          1168                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2Si(CH.sub.3).sub.3                                                            tert.-C.sub.4 H.sub.9                                                                     64-69                              1169                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2ONC(CH.sub.3).sub.2                                                           tert.-C.sub.4 H.sub.9                          1170                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2PO(OC.sub.2 H.sub.5).sub.2                                                            tert.-C.sub.4 H.sub.9                          1171                                                                             i-C.sub.3 H.sub.7                                                                         fur-2-ylmethyl  tert.-C.sub.4 H.sub.9                          1172                                                                             i-C.sub.3 H.sub.7                                                                         tetrahydrofur-2-                                                                              tert.-C.sub.4 H.sub.9                                         yl-methyl                                                      1173                                                                             i-C.sub.3 H.sub.7                                                                         pyrid-2-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                                                                     oil; 1.30(s; 6H)                                                              1.44(s; 9H),                                                                  3.40(sept; 1H)                                                                5.52(s; 2H)                                                                   7.20-8.64(m;                                                                  4H), 8.60(bs;                                                                 1H, NH)                            1174                                                                             i-C.sub.3 H.sub.7                                                                         pyrid-4-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                          1175                                                                             i-C.sub.3 H.sub.7                                                                         pyrid-3-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                          1176                                                                             i-C.sub.3 H.sub.7                                                                         thien-2-yl-methyl                                                                             tert.-C.sub.4 H.sub.9                          1177                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2N(CH.sub.3).sub.2                                                             tert.-C.sub.4 H.sub.9                          1178                                                                             i-C.sub.3 H.sub.7                                                                          ##STR35##      tert.-C.sub.4 H.sub.9                          1179                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CF.sub.3                                                                              tert.-C.sub.4 H.sub.9                          1352                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2C(CH.sub.3)CH.sub.2                                                                   tert.-C.sub.4 H.sub.9                          1153                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2 C(Cl)CH.sub.2                                                                        tert.-C.sub.4 H.sub.9                          1154                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CCCH.sub.2 OH                                                                         tert.-C.sub.4 H.sub.9                          1155                                                                             i-C.sub.3 H.sub.7                                                                          ##STR36##      tert.-C.sub.4 H.sub.9                          1156                                                                             i-C.sub.3 H.sub.7                                                                          ##STR37##      tert.-C.sub.4 H.sub.9                          1157                                                                             i-C.sub.3 H.sub.7                                                                          ##STR38##      tert.-C.sub.4 H.sub.9                          1180                                                                             i-C.sub.3 H.sub.7                                                                         phenethyl       tert.-C.sub.4 H.sub.9                          1181                                                                             i-C.sub.3 H.sub.7                                                                         CH(C.sub.6 H.sub.5)COOCH.sub.3                                                                tert.-C.sub.4 H.sub.9                          1182                                                                             i-C.sub.3 H.sub.7                                                                         piperidino      tert.-C.sub.4 H.sub.9                          1183                                                                             i-C.sub.3 H.sub.7                                                                         phthalimido     tert.-C.sub.4 H.sub.9                          1184                                                                             i-C.sub.3 H.sub.7                                                                          ##STR39##      tert.-C.sub.4 H.sub.9                          1185                                                                             i-C.sub.3 H.sub.7                                                                         NCHC.sub.6 H.sub.5                                                                            tert.-C.sub.4 H.sub.9                          1186                                                                             i-C.sub.3 H.sub.7                                                                          ##STR40##      tert.-C.sub.4 H.sub.9                          1187                                                                             i-C.sub.3 H.sub.7                                                                         CH(CH.sub.3 CH)(OCH.sub.3).sub.2                                                              tert.-C.sub.4 H.sub.9                          1188                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CON(C.sub.2 H.sub.5).sub.2                                                            tert.-C.sub.4 H.sub.9                                                                     91-93                              1189                                                                             i-C.sub.3 H.sub.7                                                                         N(C.sub.2 H.sub.5).sub.2                                                                      tert.-C.sub.4 H.sub.9                          1190                                                                             CH.sub.3    NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     108-109                            1191                                                                             CH.sub.3    cyclohexanimino tert.-C.sub.4 H.sub.9                                                                     91-92                              1192                                                                             CH.sub.3    NC(cyclo-C.sub.3 H.sub.5).sub.2                                                               tert.-C.sub.4 H.sub.9                                                                     50-52                              1193                                                                             CH.sub.3    H               N(CH.sub.3).sub.2                                                                         225-227                            1194                                                                             CH.sub.3    H               piperidino  162-164                            1195                                                                             CH.sub.3    CH.sub.2CCH     tert.-C.sub.4 H.sub.9                                                                     90-95                              1197                                                                             CH.sub.3    2-NO.sub.2 -4-FC.sub.6 H.sub.3                                                                tert.-C.sub.4 H.sub.9                                                                     oil; 1.44(s; 9H),                                                             2.59(s; 3H),                                                                  7.24 and 8.30(m;                                                              3H), 8.16(bs;                                                                 1H, NH)                            1198                                                                             CH.sub.3    3,5-(CF.sub.3).sub.2C.sub.6 H.sub.3                                                           tert.-C.sub.4 H.sub.9                                                                     156-159                            1199                                                                             CH.sub.3    H               CH.sub.3    192-197                            1200                                                                             CH.sub.3    H               OC.sub.2 H.sub.5                                                                          145-148                            1201                                                                             CH.sub.3    H               cyclo-C.sub.4 H.sub.7                                                                     141-142                            1202                                                                             CH.sub.3    H               cyclo-C.sub.3 H.sub.5                                                                     135-137                            1203                                                                             CH.sub.3    NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.3 H.sub.5                                                                     91-93                              1204                                                                             CH.sub.3    H               C.sub.2 H.sub.5                                                                           151-154                            1205                                                                             CH.sub.3    NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.4 H.sub.7                                                                     77-79                              1207                                                                             CH.sub.3    CH.sub.2 CO.sub.2 CH.sub.3                                                                    tert.-C.sub.4 H.sub.9                                                                     88-89                              1208                                                                             C.sub.2 H.sub.5                                                                           succinimido     i-C.sub.3 H.sub.7                                                                         132-136                            1209                                                                             n-C.sub.3 H.sub.7                                                                         H               cyclo-C.sub.6 H.sub.11                                                                    132-134                            1210                                                                             n-C.sub.3 H.sub.7                                                                         H               tert.-C.sub.4 H.sub.9                                                                     82-83                              1211                                                                             n-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     66-68                              1212                                                                             n-C.sub.3 H.sub.7                                                                         succinimido     tert.-C.sub.4 H.sub.9                                                                     126-129                            1213                                                                             n-C.sub.3 H.sub.7                                                                         succinimido     cyclo-C.sub.3 H.sub.5                                                                     104-106                            1214                                                                             n-C.sub. 3 H.sub.7                                                                        NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.3 H.sub.5                                                                     oil 0.70(m; 2H),                                                              0.90(m; 2H),                                                                  1.00(t; 3H),                                                                  1.78(m; 2H),                                                                  2.16 and 2.19(2s;                                                             6H), 2.92(t;                                                                  2H), 3.00(m;                                                                  1H), 9.24(bs;                                                                 1H, NH)                            1215                                                                             n-C.sub.3 H.sub.7                                                                         H               cyclo-C.sub.3 H.sub.5                                                                     104-106                            1216                                                                             n-C.sub.3 H.sub.7                                                                         H               i-C.sub.3 H.sub.7                                                                         70-71                              1217                                                                             n-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            i-C.sub.3 H.sub.7                                                                         72-73                              1218                                                                             n-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.6 H.sub.11                                                                    110-111                            1219                                                                             n-C.sub.3 H.sub.7                                                                         H               C.sub.6 H.sub.5                                                                           165-166                            1220                                                                             i-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     112-113                            1221                                                                             i-C.sub.3 H.sub.7                                                                          ##STR41##      tert.-C.sub.4 H.sub.9                                                                     83-86                              1222                                                                             i-C.sub.3 H.sub.7                                                                         cyclohexanimino tert.-C.sub.4 H.sub.9                                                                     91-94                              1223                                                                             i-C.sub.3 H.sub.7                                                                         NC(cyclo-C.sub.3 H.sub.5).sub.2                                                               tert.-C.sub.4 H.sub.9                                                                     70-75                              1224                                                                             i-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            tetrahydrofur-3-yl                                                                        104-106                            1225                                                                             i-C.sub.3 H.sub.7                                                                         succinimido     tetrahydrofur-3-yl                                                                        160-162                            1226                                                                             i-C.sub.3 H.sub.7                                                                         H               tetrahydrofur-3-yl                                                                        oil 1.33(d; 6H),                                                              2.40(m; 2H),                                                                  3.75(sept; 1H),                                                               4.00(m; 4H),                                                                  4.75(m; 1H),                                                                  8.25(d; 1H, NH)                    1227                                                                             i-C.sub.3 H.sub.7                                                                         H               OC.sub.2 H.sub.5                                                                          134-135                            1228                                                                             i-C.sub.3 H.sub.7                                                                         succinimido     OC.sub.2 H.sub.5                                                                          146-148                            1229                                                                             i-C.sub.3 H.sub.7                                                                         H               thiazol-2-yl                                                                              195                                1230                                                                             i-C.sub.3 H.sub.7                                                                         H               5-methyl-thiazol-                                                                         248                                                               2-yl                                           1231                                                                             i-C.sub.3 H.sub.7                                                                         H               5-ethyl-thiazol-                                                                          228-230                                                           2-yl                                           1232                                                                             i-C.sub.3 H.sub.7                                                                         H               5-n-propyl-thiazol-                                                                       160-163                                                           2-yl                                           1233                                                                             i-C.sub.3 H.sub.7                                                                         succinimido     tert.-C.sub.4 H.sub.9                                                                     141-144                            1234                                                                             i-C.sub.3 H.sub.7                                                                         H               cyclo-C.sub.4 H.sub.7                                                                     95-96                              1235                                                                             i-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.4 H.sub.7                                                                     100-101                            1236                                                                             i-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            N(CH.sub.3).sub.2                                                                         129-131                            1237                                                                             i-C.sub.3 H.sub.7                                                                         H               N(CH.sub.3).sub.2                                                                         163-165                            1238                                                                             i-C.sub.3 H.sub.7                                                                         H               piperidino  167-168                            1239                                                                             i-C.sub.3 H.sub.7                                                                         H               morpholino  177-179                            1240                                                                             i-C.sub.3 H.sub.7                                                                         H               cyclo-C.sub.5 H.sub.9                                                                     62-65                              1241                                                                             i-C.sub.3 H.sub.7                                                                         H               cyclopropylmethyl                                                                         88-90                              1242                                                                             i-C.sub.3 H.sub.7                                                                         H               s-C.sub.4 H.sub.9                                                                         oil; 1.00(t; 3H),                                                             1.34(d; 3H),                                                                  1.37(d; 6H),                                                                  1.66(quint; 2H),                                                              3.78(sept; 1H),                                                               4.17(m; 1H),                                                                  7.04(d, 1H, NH)                    1243                                                                             i-C.sub.3 H.sub.7                                                                         NC(CH.sub.3).sub.2                                                                            s-C.sub.4 H.sub.9                                                                         oil; 0.98(t; 3H),                                                             1.26(d, 3H),                                                                  1,39(d, 6H)                                                                   1.64(quint;                                                                   2H), 2.16 and                                                                 2.18(2s; 6H)                                                                  3.44(sept; 1H),                                                               4.10(m, 1H),                                                                  8.54(d, 1H, NH)                    1244                                                                             i-C.sub.3 H.sub.7                                                                         H               mixture of  197                                                               4-methyl-5-carboxy-                                                           thiazol-2-yl and                                                              4-methyl-thiazol-2-yl                          1245                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CHCHC.sub.6 H.sub.5                                                                   tert.-C.sub.4 H.sub.9                                                                     59-63                              1246                                                                             i-C.sub.3 H.sub.7                                                                         4-CO.sub.2 CH.sub.3 C.sub.6 H.sub.4                                                           tert.-C.sub.4 H.sub.9                                                                     143-145                            1247                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2CN                                                                            tert.-C.sub.4 H.sub.9                                                                     67-71                              1248                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CCl.sub.3                                                                             tert.-C.sub.4 H.sub.9                                                                     72-75                              1249                                                                             i-C.sub.3 H.sub.7                                                                         4-NHCOCH.sub.3C.sub.6 H.sub.4                                                                 tert.-C.sub.4 H.sub.9                                                                     212-214                            1250                                                                             i-C.sub.3 H.sub.7                                                                         2,4-Cl.sub.2C.sub.6 H.sub.3                                                                   tert.-C.sub.4 H.sub.9                                                                     140-141                            1251                                                                             i-C.sub.3 H.sub.7                                                                         cyclooctanimino tert.-C.sub.4 H.sub.9                                                                     oil, 1.37(d, 6H),                                                             1.47(s; 9H),                                                                  1.28-1.93(m;                                                                  10H), 2.54(m;                                                                 4H), 3.44(sept,                                                               1H), 8.44(bs;                                                                 1H, NH)                            1252                                                                             i-C.sub.3 H.sub.7                                                                         (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3                                                  tert.-C.sub.4 H.sub.9                                                                     oil, 1.34(d; 6H),                                                             1.47(s; 9H),                                                                  3.39(s; 3H),                                                                  3.45(sept; 1H),                                                               3.60(m; 4H),                                                                  3.84 and 4.50(m;                                                              4H), 8.94(bs;                                                                 1H, NH)                            1253                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2SCH.sub.3                                                                     tert.-C.sub.4 H.sub.9                                                                     46-48                              1254                                                                             i-C.sub.3 H.sub.7                                                                         Pyrid-2-yl      tert.-C.sub.4 H.sub.9                                                                     155-163                            1255                                                                             i-C.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2Cl                                                                            tert.-C.sub.4 H.sub.9                                                                     70-72                              1263                                                                             n-C.sub.4 H.sub.9                                                                         H               CH.sub.3    146-149                            1264                                                                             n-C.sub.4 H.sub.9                                                                         H               i-C.sub.3 H.sub.7                                                                         60-63                              1265                                                                             n-C.sub.4 H.sub.9                                                                         H               cyclo-C.sub.3 H.sub.5                                                                     112-114                            1266                                                                             n-C.sub.4 H.sub.9                                                                         H               C.sub.6 H.sub.5                                                                           145-150                            1267                                                                             n-C.sub.4 H.sub.9                                                                         H               tert.-C.sub.4 H.sub.9                                                                     52-54                              1268                                                                             n-C.sub.4 H.sub.9                                                                         NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     58-62                              1269                                                                             n-C.sub.4 H.sub.9                                                                         CH.sub.2 CCl.sub.3                                                                            tert.-C.sub.4 H.sub.9                                                                     oil 0.92(t; 3H),                                                              1.43(m, 2H),                                                                  1.48(s; 9H),                                                                  1.74(m; 2H)                                                                   3.00(t; 2H),                                                                  5.01(s; 2H),                                                                  8.80(bs; 1H; NH)                   1270                                                                             n-C.sub.4 H.sub.9                                                                         2,6-Br.sub.2 -4-CNC.sub.6 H.sub.2                                                             tert.-C.sub.4 H.sub.9                                                                     165-170                            1271                                                                             n-C.sub.4 H.sub.9                                                                         CH.sub.2CHCH.sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     oil 0.92(t; 3H),                                                              1.41(m; 2H),                                                                  1.46(s; 9H),                                                                  1.66(m; 2H),                                                                  2.89(t; 2H),                                                                  4.88(d; 2H),                                                                  5.40(m; 2H),                                                                  6.01(m; 1H),                                                                  9.19(bs; 1H, NH)                   1272                                                                             n-C.sub.4 H.sub.9                                                                         2,4-dichlorobenzyl                                                                            tert.-C.sub.4 H.sub.9                                                                     81-86                              1273                                                                             n-C.sub.4 H.sub.9                                                                         H               cyclopropylmethyl                                                                         65-70                              1274                                                                             s-C.sub.4 H.sub.9                                                                         H               i-C.sub.3 H.sub.7                                                                         oil 0.92(t, 3H),                                                              1.34(d, 3H),                                                                  1.39(d; 6H),                                                                  1.76(m; 2H),                                                                  3.65(m; 1H),                                                                  4.32(m; 1H),                                                                  7.08(bs; 1H, NH)                   1275                                                                             s-C.sub.4 H.sub.9                                                                         NC(CH.sub.3).sub.2                                                                            i-C.sub.3 H.sub.7                                                                         80-84                              1276                                                                             s-C.sub.4 H.sub.9                                                                         H               cyclo-C.sub.3 H.sub.7                                                                     78-85                              1277                                                                             s-C.sub.4 H.sub.9                                                                         NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.3 H.sub.5                                                                     oil 0.70(m,; 2H),                                                             0.90(m; 2H),                                                                  0.92(t; 3H),                                                                  1.34(d; 3H),                                                                  1.79(m; 2H),                                                                  2.14 and 2.18(2s;                                                             6H), 2.97(m;                                                                  1H), 3.24(m;                                                                  1H), 8.80(bs,                                                                 1H, NH)                            1278                                                                             s-C.sub.4 H.sub.9                                                                         succinimido     cyclo-C.sub.3 H.sub.5                                                                     112-115                            1279                                                                             s-C.sub.4 H.sub.9                                                                         H               tert.-C.sub.4 H.sub.9                                                                     93-95                              1280                                                                             s-C.sub.4 H.sub.9                                                                         NC(CH.sub.3).sub.2                                                                            tert.-C.sub. 4 H.sub.9                                                                    oil 0.92(t, 3H),                                                              1.34(d; 3H),                                                                  1.48(s; 9H),                                                                  1.80(m; 2H),                                                                  2.12 and 2.16(2s;                                                             6H), 3.26(m,                                                                  1H), 8.29(bs,                                                                 1H, NH)                            1281                                                                             s-C.sub.4 H.sub.9                                                                         H               C.sub.6 H.sub.5                                                                           117-120                            1282                                                                             s-C.sub.4 H.sub.9                                                                         NC(CH.sub.3).sub.2                                                                            C.sub.6 H.sub.5                                                                           oil, 0.93(t; 3H),                                                             1.36(d; 3H),                                                                  1.80(m; 2H),                                                                  2.14 and 2.18(2s;                                                             6H), 3.28(m;                                                                  1H),                                                                          7.10-7.80(m; 5H)                                                              10.90(bs; 1H), NH)                 1283                                                                             tert.-C.sub.4 H.sub.9                                                                     succinimido     i-C.sub.3 H.sub.7                                                                         137-140                            1284                                                                             tert.-C.sub.4 H.sub.9                                                                     succinimido     4-ClC.sub.6 H.sub.4                                                                       238-242                            1285                                                                             tert.-C.sub.4 H.sub.9                                                                     succinimido     tert.-C.sub.4 H.sub.9                                                                     144-146                            1286                                                                             tert.-C.sub.4 H.sub.9                                                                     NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     86-90                              1287                                                                             tert.-C.sub.4 H.sub.9                                                                     H               cyclo-C.sub.3 H.sub.5                                                                     75-77                              1288                                                                             tert.-C.sub.4 H.sub.9                                                                     NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.3 H.sub.5                                                                     93-98                              1290                                                                             neo-C.sub.5 H.sub.11                                                                      H               CH.sub.3    130-133                            1291                                                                             neo-C.sub.5 H.sub.11                                                                      H               i-C.sub.3 H.sub.7                                                                         100-104                            1292                                                                             neo-C.sub.5 H.sub.11                                                                      H               cyclo-C.sub.3 H.sub.5                                                                     133-136                            1293                                                                             neo-C.sub.5 H.sub.11                                                                      NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.3 H.sub.5                                                                     56-62                              1294                                                                             neo-C.sub.5 H.sub.11                                                                      H               tert.-C.sub.4 H.sub.9                                                                     112-117                            1295                                                                             neo-C.sub.5 H.sub.11                                                                      NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     107-111                            1296                                                                             neo-C.sub.5 H.sub.11                                                                      H               C.sub.6 H.sub.5                                                                           205-207                            1297                                                                             cyclo-C.sub.3 H.sub.5                                                                     succinimido     i-C.sub.3 H.sub.7                                                                         131-133                            1298                                                                             cyclo-C.sub.3 H.sub.5                                                                     succinimido     tert.-C.sub.4 H.sub.9                                                                     167-168                            1299                                                                             cyclo-C.sub.3 H.sub.5                                                                     succinimido     C.sub.6 H.sub.5                                                                           168-170                            1300                                                                             cyclo-C.sub.3 H.sub.5                                                                     H               cyclo-C.sub.3 H.sub.5                                                                     139-140                            1301                                                                             cyclo-C.sub.3 H.sub.5                                                                     NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.3 H.sub.5                                                                     oil 0.80(m; 8H),                                                              2.02 and 2.04(2s;                                                             6H), 2.30(m;                                                                  1H), 2.86(m;                                                                  1H), 9.20(d;                                                                  1H, NH)                            1302                                                                             cyclo-C.sub.3 H.sub.5                                                                     NC(cyclo-       cyclo-C.sub.3 H.sub.7                                                                     106-108                                           C.sub.3 H.sub.5).sub.2                                         1303                                                                             cyclo-C.sub.3 H.sub.5                                                                     H               cyclo-C.sub.5 H.sub.9                                                                     106-109                            1304                                                                             cyclo-C.sub.3 H.sub.5                                                                     NC(CH.sub.3).sub.2                                                                            cyclo-C.sub.5 H.sub.9                                                                     125-127                            1305                                                                             cyclo-C.sub.5 H.sub.9                                                                     H               C.sub.6 H.sub.5                                                                           170-171                            1306                                                                             cyclo-C.sub.5 H.sub.9                                                                     H               cyclo-C.sub.3 H.sub.5                                                                     118-120                            1307                                                                             cyclo-C.sub.5 H.sub.9                                                                     NC(CH.sub.3 ).sub.2                                                                           cyclo-C.sub.3 H.sub.5                                                                     55-57                              1308                                                                             cyclo-C.sub.5 H.sub.9                                                                     NC(CH.sub.3).sub.2                                                                            CH.sub.3    100-101                            1309                                                                             cyclo-C.sub.5 H.sub.9                                                                     H               CH.sub.3    166-167                            1310                                                                             cyclo-C.sub.5 H.sub.9                                                                     H               tert.-C.sub.4 H.sub.9                                                                     125-126                            1311                                                                             cyclo-C.sub.5 H.sub.9                                                                     NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     112-114                            1312                                                                             tetrahydro- succinimido     C.sub.6 H.sub.5                                                                           80                                    pyran-3-yl                                                                 1313                                                                             2-CH.sub.3 OC.sub.6 H.sub.4                                                               H               tert.-C.sub.4 H.sub.9                                                                     179-184                            1314                                                                             2-CH.sub.3 OC.sub.6 H.sub.4                                                               H               cyclo-C.sub.4 H.sub.5                                                                     177-180                            1315                                                                             2,6F.sub.2C.sub.6 H.sub.3                                                                 H               tert.-C.sub.4 H.sub.9                                                                     128-135                            1316                                                                             2,6F.sub.2C.sub.6 H.sub.3                                                                 H               cyclo-C.sub.3 H.sub.5                                                                     134-138                            1317                                                                             CH.sub.3O   H               tert.-C.sub.4 H.sub.9                                                                     oil 1.52(s; 9H),                                                              4.12(s; 3H),                                                                  7.16(bs; 1H, NH)                   1318                                                                             CH.sub.3OCH.sub.2                                                                         H               tert.-C.sub.4 H.sub.9                                                                     95-100                             1319                                                                             CH.sub.3OCH.sub.2                                                                         H               cyclo-C.sub.3 H.sub.5                                                                     90-95                              1320                                                                             CH.sub.3OCH.sub.2                                                                         NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                     65-70                              1321                                                                             CH.sub.3OCH(CH.sub.3)                                                                      NC(CH.sub.3).sub.2                                                                           tert.-C.sub.4 H.sub.9                                                                     oil 1.45(s; 9H)                                                               1.60(d; 3H),                                                                  2.16 and 2.18(2s;                                                             6H); 3.34(s;                                                                  3H), 4.87(quart.;                                                             1H) 8.10(bs;                                                                  1H, NH)                            1322                                                                             CH.sub.3OCH(CH.sub.3)                                                                     H               tert.-C.sub.4 H.sub.9                                                                     69-71                              1323                                                                             CH.sub.3OCH(CH.sub.3)                                                                     2,6-Br.sub.2 -4-CNC.sub.6 H.sub.2                                                             tert.-C.sub.4 H.sub.9                                                                     118-120                            1324                                                                             CH.sub.3    CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                 tert.-C.sub.4 H.sub.9                                                                     oil 1.46(s; 9H)                                                               2.54(s; 3H)                                                                   3.82(s; 3H),                                                                  5.40(quart.; 1H)                                                              9.00(bs, 1H, NH)                   1325                                                                             CH.sub.3    2,6-Br.sub.2 -4-CNC.sub.6 H.sub.2                                                             tert.-C.sub.4 H.sub.9                                                                     143-146                            1326                                                                              ##STR42##  H               tert.-C.sub.4 H.sub.9                                                                     168-170                            1327                                                                              ##STR43##  H               tert.-C.sub.4 H.sub.9                                                                     157                                1328                                                                              ##STR44##  H               tert.-C.sub.4 H.sub.9                                                                     254                                1329                                                                              ##STR45##  CH.sub.3        tert.-C.sub.4 H.sub.9                                                                     oil 1.5(s, 9H) 3.8; (s; 3H),                                                  3.9(s; 3H), 6.5(d; 1H), 7.6(d;                                                1H), 8.7(bs, 1H, NH)               1330                                                                              ##STR46##  CH.sub.3        tert.-C.sub.4 H.sub.9                                                                     120-122° C.                 1331                                                                              ##STR47##  CH.sub.3        tert.-C.sub.4 H.sub.9                                                                     oil, 1.5(s; 9H), 3.7(s; 3H),                                                  3.8(s; 3H), 3.9(s, 3H), 8.0(s;                                                1H), 9.2(bs, 1H, NH)               1332                                                                              ##STR48##  H               tert.-C.sub.4 H.sub.9                          1333                                                                              ##STR49##  NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                          1334                                                                              ##STR50##  H               tert.-C.sub.4 H.sub.9                          1335                                                                              ##STR51##  NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                          1336                                                                             pyrid-2-yl  H               tert.-C.sub.4 H.sub.9                          1337                                                                             pyrid-2-yl  NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                          1338                                                                             pyrid-3-yl  H               tert.-C.sub.4 H.sub.9                          1339                                                                             pyrid-3-yl  NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                          1340                                                                             pyrid-4-yl  H               tert.-C.sub.4 H.sub.9                          1341                                                                             pyrid-4-yl  NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                          1342                                                                             4-FC.sub.6 H.sub.4CH.sub.2                                                                H               tert.-C.sub.4 H.sub.9                          1343                                                                             4-FC.sub.6 H.sub.4CH.sub.2                                                                NC(CH.sub.3).sub.2                                                                            tert.-C.sub.4 H.sub.9                          1344                                                                             CH.sub.3    n-C.sub.4 H.sub.9                                                                             tert.-C.sub.4 H.sub.9                          1345                                                                             CH.sub.3    C.sub.6 H.sub.5 tert.-C.sub.4 H.sub.9                          1346                                                                             CH.sub.3    tert.-C.sub.4 H.sub.9                                                                         tert.-C.sub.4 H.sub.9                          1347                                                                             C.sub.2 H.sub.5                                                                           n-C.sub.4 H.sub.9                                                                             tert.-C.sub.4 H.sub.9                          1348                                                                             C.sub.2 H.sub.5                                                                           C.sub.6 H.sub.5 tert.-C.sub.4 H.sub.9                          1349                                                                             i-C.sub.3 H.sub.7                                                                         n-C.sub.4 H.sub.9                                                                             tert.-C.sub.4 H.sub.9                          1350                                                                             i-C.sub.3 H.sub.7                                                                         C.sub.6 H.sub.5                                                1351                                                                             i-C.sub.3 H.sub.7                                                                         cyclopentanimino                                                                              tert.-C.sub.4 H.sub.9                                                                     113-115                            __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                         ##STR52##                                                                                                    mp [°C.]/.sup.1 H-NMR                  No.  R.sup.1  R.sup.5   R.sup.4 (CDCl.sub.3) [ppm]                            ______________________________________                                        2001 CH.sub.3 n-C.sub.4 H.sub.9                                                                       tert.-C.sub.4 H.sub.9                                 2002 CH.sub.3 C.sub.6 H.sub.5                                                                         tert.-C.sub.4 H.sub.9                                 2003 CH.sub.3 tert.-C.sub.4 H.sub.9                                                                   tert.-C.sub.4 H.sub.9                                                                 oil; 1.46(s; 9H)                                                              1.60(s; 9H),                                                                  2.50(s; 3H),                                                                  7.94(bs;                                                                      1H, NH)                                       2004 C.sub.2 H.sub.5                                                                        n-C.sub.4 H.sub.9                                                                       tert.-C.sub.4 H.sub.9                                 2005 C.sub.2 H.sub.5                                                                        C.sub.6 H.sub.5                                                                         tert.-C.sub.4 H.sub.9                                 2006 i-C.sub.3 H.sub.7                                                                      C.sub.6 H.sub.5                                                                         tert.-C.sub.4 H.sub.9                                 2007 i-C.sub.3 H.sub.7                                                                      n-C.sub.4 H.sub.9                                                                       tert.-C.sub.4 H.sub.9                                 ______________________________________                                    

                                      TABLE 3                                     __________________________________________________________________________     ##STR53##                                                                                                  mp [°C.]/H-NMR                           No. R.sup.1                                                                            R.sup.5      R.sup.4 (CDCl.sub.3) [ppm]                              __________________________________________________________________________    3001                                                                              CH.sub.3                                                                           H            i-C.sub.3 H.sub.7                                                                     153-154                                         3002                                                                              CH.sub.3                                                                           H            tert.-C.sub.4 H.sub.9                                                                 158-159                                         3003                                                                              CH.sub.3                                                                           H            C.sub.6 H.sub.5                                                                       178-183                                         3004                                                                              CH.sub.3                                                                           H            4-ClC.sub.6 H.sub.4                                                                   231                                             3005                                                                              CH.sub.3                                                                           H            3-CF.sub.3C.sub.6 H.sub.4                                                             221-223                                         3006                                                                              C.sub.2 H.sub.5                                                                    H            i-C.sub.3 H.sub.7                                                                     138-140                                         3007                                                                              C.sub.2 H.sub.5                                                                    CH.sub.3     i-C.sub.3 H.sub.7                                                                     55-56                                           3008                                                                              C.sub.2 H.sub.5                                                                    H            tert.-C.sub.4 H.sub.9                                                                 155-157                                         3009                                                                              C.sub.2 H.sub.5                                                                    CH.sub.3     tert.-C.sub.4 H.sub.9                                                                  39                                             3010                                                                              C.sub.2 H.sub.5                                                                    H            C.sub.6 H.sub.5                                                                       164                                             3011                                                                              C.sub.2 H.sub.5                                                                    CH.sub.3     C.sub.6 H.sub.5                                                                       130-131                                         3012                                                                              C.sub.2 H.sub.5                                                                    H            4-ClC.sub.6 H.sub.4                                                                   202-204                                         3013                                                                              C.sub.2 H.sub.5                                                                    CH.sub.3     4-ClC.sub.6 H.sub.4                                                                   158-159                                         3014                                                                              C.sub.2 H.sub.5                                                                    H            3-CF.sub.3C.sub.6 H.sub.4                                                             191-195                                         3015                                                                              C.sub.2 H.sub.5                                                                    CH.sub.3     3-CF.sub.3C.sub.6 H.sub.4                                                              84                                             3016                                                                              i-C.sub.3 H.sub.7                                                                  H            i-C.sub.3 H.sub.7                                                                     160-162                                         3017                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3     i-C.sub.3 H.sub.7                                                                     90-91                                           3018                                                                              i-C.sub.3 H.sub.7                                                                  H            tert.-C.sub.4 H.sub.9                                                                 178-179                                         3019                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3     tert.-C.sub.4 H.sub.9                                                                 38-41                                           3020                                                                              i-C.sub.3 H.sub.7                                                                  H            C.sub.6 H.sub.5                                                                       171-172                                         3021                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3     C.sub.6 H.sub.5                                                                       92-93                                           3022                                                                              i-C.sub.3 H.sub.7                                                                  H            4-ClC.sub.6 H.sub.4                                                                   185-186                                         3023                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3     4-ClC.sub.6 H.sub.4                                                                   92-93                                           3024                                                                              i-C.sub.3 H.sub.7                                                                  H            3-CF.sub.3C.sub.6 H.sub.4                                                             177-179                                         3025                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3     3-CF.sub.3C.sub.6 H.sub.4                                                             37-45                                           3026                                                                              C.sub.6 H.sub.5                                                                    H            i-C.sub.3 H.sub.7                                                                     144                                             3027                                                                              C.sub.6 H.sub.5                                                                    CH.sub.3     i-C.sub.3 H.sub.7                                                                      98- 100                                        3028                                                                              C.sub.6 H.sub.5                                                                    H            tert.-C.sub.4 H.sub.9                                                                 209                                             3029                                                                              C.sub.6 H.sub.5                                                                    CH.sub.3     tert.-C.sub.4 H.sub.9                                                                 130-131                                         3030                                                                              C.sub.6 H.sub.5                                                                    H            C.sub.6 H.sub.5                                                                       204                                             3031                                                                              C.sub.6 H.sub.5                                                                    CH.sub.3     C.sub.6 H.sub.5                                                                       100-101                                         3032                                                                              C.sub.6 H.sub.5                                                                    H            4-ClC.sub.6 H.sub.4                                                                   209                                             3033                                                                              C.sub.6 H.sub.5                                                                    CH.sub.3     4-ClC.sub.6 H.sub.4                                                                   157-158                                         3034                                                                              C.sub.6 H.sub.5                                                                    H            3-CF.sub.3C.sub.6 H.sub.4                                                             217                                             3035                                                                              C.sub.6 H.sub.5                                                                    CH.sub.3     3-CF.sub.3C.sub.6 H.sub.4                                                             131-132                                         3036                                                                              i-C.sub.3 H.sub.7                                                                  succinimido  i-C.sub.3 H.sub.7                                                                      98-100                                         3037                                                                              i-C.sub.3 H.sub.7                                                                  succinimido  tert.-C.sub.4 H.sub.9                                                                 75-76                                           3038                                                                              i-C.sub.3 H.sub.7                                                                  Na.sup.⊕ tert.-C.sub.4 H.sub.9                                                                 300                                             3039                                                                              i-C.sub.3 H.sub.7                                                                  K.sup.⊕  tert.-C.sub.4 H.sub.9                                                                 110                                             3040                                                                              i-C.sub.3 H.sub.7                                                                  Na.sup.⊕ C.sub.6 H.sub.5                                                                       330                                             3041                                                                              i-C.sub.3 H.sub.7                                                                  K.sup.⊕  C.sub.6 H.sub.5                                                                       300                                             3042                                                                              i-C.sub.3 H.sub.7                                                                   ##STR54##   C.sub.6 H.sub. 5                                                                      154-157                                         3043                                                                              i-C.sub.3 H.sub.7                                                                   ##STR55##   C.sub.6 H.sub.5                                                                       162-164                                         3044                                                                              i-C.sub.3 H.sub.7                                                                  succinimido  C.sub.6 H.sub.5                                                                       161                                             3045                                                                              CH.sub.3                                                                           NC(CH.sub.3).sub.2                                                                         tert.-C.sub.4 H.sub.9                                                                 97-98                                           __________________________________________________________________________

Other compounds, for instance, having the general structure ##STR56##may be prepared analogously in which X and Y are oxygen or sulfur, e.g.,R¹ is a radical from the group Q1 to Q61,

R⁵ is a radical from the group M1 to M78,

R³ is a radical from the group P₁ -P₁₁

R⁴ is a radical from the group L1 to L195, and

the radicals X, Y, P, Q, M and L may be combined at will.

R¹, R⁵, R³ and R⁴ may for example denote the following radicals:

    ______________________________________                                        Comp                                                                          No.           R.sup.1                                                         ______________________________________                                        Q1            H                                                               Q2            CH.sub.3                                                        Q3            C.sub.2 H.sub.5                                                 Q4            n-C.sub.3 H.sub.7                                               Q5            i-C.sub.3 H.sub.7                                               Q6            n-C.sub.4 H.sub.9                                               Q7            i-C.sub.4 H.sub.9                                               Q8            s-C.sub.4 H.sub.9                                               Q9            tert.-C.sub.4 H.sub.9                                           Q10           cyclo-C.sub.3 H.sub.5                                           Q11           cyclo-C.sub.4 H.sub.7                                           Q12           cyclo-C.sub.5 H.sub.9                                           Q13           cyclo-C.sub.6 H.sub.11                                          Q14           cyclo-C.sub.7 H.sub.13                                          Q15           cyclo-C.sub.8 H.sub.15                                          Q16           CF.sub.3                                                        Q17           CH.sub.2 OCH.sub.3                                              Q18           CH(CH.sub.3)OCH.sub.3                                           Q19           CH(CH.sub.3)CH.sub.2 OCH.sub.3                                  Q20           CH.sub.2 OC.sub.2 H.sub.5                                       Q21           tetrahydrofur-2-yl                                              Q22           tetrahydrofur-2-yl                                              Q23           tetrahydrofur-2-yl                                              Q24           tetrahydropyran-3-yl                                            Q25           tetrahydropyran-3-yl                                            Q26           C.sub.6 H.sub.5                                                 Q27           2-FC.sub.6 H.sub.4                                              Q28           3-FC.sub.6 H.sub.4                                              Q29           4-FC.sub.6 H.sub.4                                              Q30           2-ClC.sub.6 H.sub.4                                             Q31           3-ClC.sub.6 H.sub.4                                             Q32           4-ClC.sub.6 H.sub.4                                             Q33           2-CH.sub.3C.sub.6 H.sub.4                                       Q34           3-CH.sub.3C.sub.6 H.sub.4                                       Q35           4-CH.sub.3C.sub.6 H.sub.4                                       Q36           2-CF.sub.3C.sub.6 H.sub.4                                       Q37           3-CF.sub.3C.sub.6 H.sub.4                                       Q38           4-CF.sub.3C.sub.6 H.sub.4                                       Q39           2-OCH.sub.3C.sub.6 H.sub.4                                      Q40           3-OCH.sub.3C.sub.6 H.sub.4                                      Q41           4-OCH.sub.3C.sub.6 H.sub.4                                      Q42           4-OCF.sub.3C.sub.6 H.sub.4                                      Q43           4-SCH.sub.3C.sub.6 H.sub.4                                      Q44           4-SCF.sub.3C.sub.6 H.sub.4                                      Q45           4-NO.sub.2C.sub.6 H.sub.4                                       Q46           4-CNC.sub.6 H.sub.4                                             Q47           neo-C.sub.5 H.sub.11                                            Q48           CH.sub.3 O                                                      Q49           C.sub.2 H.sub.5 O                                               Q50           C.sub.6 H.sub.5CH.sub.2                                         Q51           4-FC.sub.6 H.sub.4CH.sub.2                                      Q51           4-CH.sub.3C.sub.6 H.sub.4CH.sub.2                               Q52                                                                                          ##STR57##                                                      Q53                                                                                          ##STR58##                                                      Q54                                                                                          ##STR59##                                                      Q55                                                                                          ##STR60##                                                      Q56                                                                                          ##STR61##                                                      Q57                                                                                          ##STR62##                                                      Q58                                                                                          ##STR63##                                                      Q59           pyrid-2-yl                                                      Q60           pyrid-3-yl                                                      Q61           pyrid-4-yl                                                      Q62           2,6-F.sub.2C.sub.6 H.sub.3                                      ______________________________________                                        Comp.                                                                         No.           R.sup.5                                                         ______________________________________                                        M1            H                                                               M2            CH.sub.3                                                        M3            C.sub.2 H.sub.5                                                 M4            n-C.sub.3 H.sub.7                                               M5            i-C.sub.3 H.sub.7                                               M6            n-C.sub.4 H.sub.9                                               M7            s-C.sub.4 H.sub.9                                               M8            t-C.sub.4 H.sub.9                                               M9            CH(CH.sub.3)C.sub.6 H.sub.13                                    M10           CH.sub.2 CH.sub.2 OCH.sub.3                                     M11           CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                              M12           succinimido                                                     M13           Li.sup.⊕                                                    M14           Na.sup.⊕                                                    M15           K.sup.⊕                                                     M16           NH.sub.4.sup.⊕                                              M17           H.sub.3 N.sup.⊕ i-C.sub.3 H.sub.7                           M18           H.sub.2 N.sup.⊕ (i-C.sub.3 H.sub.7).sub.2                   M19           H.sub.3 N.sup.⊕ CH.sub.2 CH.sub.2 OH                        M20           CH.sub.2 CHCH.sub.2                                             M21           CH.sub.2C(CH.sub.3)CH.sub.2                                     M22           CH.sub.2C(Cl)CH.sub.2                                           M23           CH.sub.2CCH                                                     M24           CH.sub.2C CCH.sub.2 OH                                          M25           NC(CH.sub.3).sub.2                                              M26           NC(C.sub.2 H.sub.5).sub.2                                       M27           CH.sub.2CH.sub.2N(CH.sub.3).sub.2                               M28           CH.sub.2CH.sub.2N(C.sub.2 H.sub.5).sub.2                        M29           CH.sub.2CH.sub.2 N.sup.⊕ (CH.sub.3).sub.3 I.sup..crclbar                  .                                                               M30           CH.sub.2CF.sub.3                                                M31           phenyl                                                          M32           phenylethyl                                                     M33           CH.sub.2CH.sub.2Si(CH.sub.3).sub.3                              M34           CH.sub.2CH.sub.2ONC(CH.sub.3).sub.2                             M35           CH.sub.2PO(OC.sub.2 H.sub.5).sub.2                              M36           CH(CH.sub.3)CH(OCH.sub.3).sub.2                                 M37           CH.sub.2CON(C.sub.2 H.sub.5).sub.2                              M38           N(C.sub.2 H.sub.5).sub.2                                        M39           CH.sub.OCH.sub.2C.sub.6 H.sub.5                                 M40           CH(COOCH.sub.3).sub.2                                           M41           NC(cyclo-C.sub.3 H.sub.5).sub.2                                 M42                                                                                          ##STR64##                                                      M43           cyclohexanimino                                                 M44           cyclooctanimino                                                 M45           CH.sub.2CH.sub.2Cl                                              M46           CH.sub.2CH.sub.2CN                                              M47           CH.sub.2CCl.sub.3                                               M48           pyrid-3-ylmethyl                                                M49           thien-2-yl-methyl                                               M50                                                                                          ##STR65##                                                      M51                                                                                          ##STR66##                                                      M52                                                                                          ##STR67##                                                      M53           CH(C.sub.6 H.sub.5)COOCH.sub.3                                  M54           cyclo-C.sub.6 H.sub.11                                          M55           CH.sub.2OCH.sub.2C.sub.6 H.sub.5                                M56           tetrahydropyran-2-yl                                            M57           tetrahydrofur-2-yl                                              M58           (4-bromobenzoyl)methyl                                          M59           (4-methoxybenzoyl)methyl                                        M60           CH(COOCH.sub.3).sub.2                                           M61           phthalimidomethyl                                               M62           fur-2-ylmethyl                                                  M63           tetrahydrofur-2-yl-methyl                                       M64           pyrid-2-ylmethyl                                                M65           pyrid-4-ylmethyl                                                M66           pyrid-3-yl-methyl                                               M67           thien-2-yl-methyl                                               M68           CH(C.sub.6 H.sub.5)COOCH.sub.3                                  M69           piperidino                                                      M70           phthalimido                                                     M71                                                                                          ##STR68##                                                      M72           NCHC.sub.6 H.sub.5                                              M73                                                                                          ##STR69##                                                      M74           2-NO.sub.2 -4-FC.sub.6 H.sub.3                                  M75           3,5-(CF.sub.3).sub.2C.sub.6 H.sub.3                             M76           CH.sub.2CH.sub.2SCH.sub.3                                       M77           4-NHCOCH.sub.3C.sub.6 H.sub.4                                   M78           2,4-dichlorobenzyl                                              ______________________________________                                        Comp.                                                                         No.           R.sup.3                                                         ______________________________________                                        P1            H                                                               P2            CH.sub.3                                                        P3            C.sub.2 H.sub.5                                                 P4            n-C.sub.3 H.sub.7                                               P5            i-C.sub.3 H.sub.7                                               P6            n-C.sub.4 H.sub.9                                               P7            s-C.sub.4 H.sub.9                                               P8            t-C.sub.4 H.sub.9                                               P9            CH.sub.2CH.sub.2 OH                                             P10           CH.sub.2CH.sub.2 Cl                                             P11           CH.sub.2 OCH.sub.3                                              P12           CH.sub.2 OC.sub.2 H.sub.5                                       P13           CH.sub.2 CH.sub.2 OCH.sub.3                                     P14           CH.sub.2 SCH.sub.3                                              P15           CH.sub.2 SC.sub.2 H.sub.5                                       P16           CH.sub.2 CH.sub.2 SCH.sub.3                                     P17           CH.sub.2CH.sub.2N(CH.sub.3).sub.2                               P18           CH.sub.2 CH.sub.2N(C.sub.2 H.sub.5).sub.2                       P19           cyclo-C.sub.3 H.sub.5                                           P20           cyclo-C.sub.6 H.sub.11                                          P21           1-methyl-cyclo-C.sub.6 H.sub.10                                 ______________________________________                                        Comp.                                                                         No.           R.sup.4                                                         ______________________________________                                        L1            H                                                               L2            CH.sub.3                                                        L3            C.sub.2 H.sub.5                                                 L4            n-C.sub.3 H.sub.7                                               L5            i-C.sub.3 H.sub.6                                               L6            n-C.sub.4 H.sub.9                                               L7            i-C.sub.4 H.sub.9                                               L8            sec-C.sub.4 H.sub.9                                             L9            tert.-C.sub.4 H.sub.9                                           L10           n-C.sub.5 H.sub.11                                              L11           CH(CH.sub.3)C.sub.3 H.sub.6                                     L12           CH(C.sub.2 H.sub.5)C.sub.2 H.sub.5                              L13           n-C.sub.6 H.sub.13                                              L14           CH(CH.sub.3)C.sub.4 H.sub.9                                     L15           CH(C.sub.2 H.sub.5)C.sub.3 H.sub.7                              L16           n-C.sub.7 H.sub.15                                              L17           CH(CH.sub.3)C.sub.5 H.sub.11                                    L18           CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                              L19           n-C.sub.8 H.sub.17                                              L20           CH(CH.sub.3)C.sub.6 H.sub.13                                    L21           CH(C.sub.2 H.sub.5)C.sub.5 H.sub.11                             L22           C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3                    L23           cyclo-C.sub.3 H.sub.5                                           L24           cyclo-C.sub.4 H.sub.7                                           L25           cyclo-C.sub.5 H.sub.9                                           L26           cyclo-C.sub.6 H.sub.11                                          L27           cyclo-C.sub.7 H.sub.13                                          L28           cyclo-C.sub.8 H.sub.15                                          L29           1-methylcyclohexyl                                              L30           1-ethylcyclohexyl                                               L31           3,5-dimethylcyclohexyl                                          L32           3-trifluoromethylcyclohexyl                                     L33           tetrahydropyran-4-yl                                            L34           4-methyl-tetrahydropyran                                        L35           4-methyl-tetrahydropyran-4-yl                                   L36           CH.sub.2CHCH.sub.2                                              L37           CH(CH.sub.3)CHCH.sub.2                                          L38           C(CH.sub.3).sub.2 CHCH.sub.2                                    L39           C(CH.sub.3,C.sub.2 H.sub.5)CHCH.sub.2                           L40           C(CH.sub.3).sub.2C.sub.2 H.sub.5                                L41           C(CH.sub.3,C.sub.2 H.sub.5)C.sub.2 H.sub.5                      L42           C(CH.sub.3).sub.2 C.sub.3 H.sub.7                               L43           C(CH.sub.3).sub.2 cycloC.sub.6 H.sub.11                         L44           CH.sub.2 C(CH.sub.3)CH.sub.2                                    L45           CH.sub.2 CHCHCH.sub.3                                           L46           CH(CH.sub.3)CHCHCH.sub.3                                        L47           C(CH.sub.3).sub.2 CHCHCH.sub.3                                  L48           CH.sub.2 CCH                                                    L49           CH(CH.sub.3)CCH                                                 L50           C(CH.sub.3).sub.2 CCH                                           L51           C(CH.sub.3,C.sub.2 H.sub.5)CCH                                  L52           C(C.sub.2 H.sub.5).sub.2 CCH                                    L53           CH.sub.2 CCCH.sub.3                                             L54           CH(CH.sub.3)CCCH.sub.3                                          L55           C(CH.sub.3).sub.2 CCCH.sub.3                                    L56           CH.sub.2 C.sub.6 H.sub.5                                        L57           CH(CH.sub.3)C.sub.6 H.sub.5                                     L58           C(CH.sub.3).sub.2 C.sub.6 H.sub.5                               L59           CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                               L60           CH.sub.2 CH.sub.2 SCH.sub.3                                     L61           CH(CH.sub.3)CH.sub.2 SCH.sub.3                                  L62           C(CH.sub.3).sub.2 CH.sub.2 SCH.sub.3                            L63           CH.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                            L64           CH.sub.2 CH.sub.2 Cl                                            L65           CH(CH.sub.3)CH.sub.2 Cl                                         L66           C(CH.sub.3).sub.2 CH.sub.2 Cl                                   L67           CH.sub.2 CH.sub.2 OCH.sub.3                                     L68           CH(CH.sub.3)CH.sub.2 OCH.sub.3                                  L69           C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                            L70           CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                             L71           CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2                      L72           CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                            L73           CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                    L74           CH.sub.2 CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2             L75           2-CH.sub.3C.sub.6 H.sub.4                                       L76           3-CH.sub.3C.sub.6 H.sub.4                                       L77           4-CH.sub.3C.sub.6 H.sub.4                                       L78           2-C.sub.2 H.sub.5C.sub.6 H.sub.4                                L79           3-C.sub.2 H.sub.5C.sub.6 H.sub.4                                L80           4-C.sub.2 H.sub.5C.sub.6 H.sub.4                                L81           3-tert.-C.sub.4 H.sub.9C.sub.6 H.sub.4                          L82           4-tert.-C.sub.4 H.sub.9C.sub.6 H.sub.4                          L83           2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                             L84           2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                             L85           2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                             L86           2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3                             L87           3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                             L88           3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                             L89           2,3,4-(CH.sub.3).sub.3C.sub.6 H.sub.2                           L90           2,3,5-(CH.sub.3).sub.3C.sub.6 H.sub.2                           L91           2,4,5-(CH.sub.3).sub.3C.sub.6 H.sub.2                           L92           2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                           L93           3,4,5-(CH.sub.3).sub.3C.sub.6 H.sub.2                           L94           2-CF.sub.3C.sub.6 H.sub.4                                       L95           3-CF.sub.3C.sub.6 H.sub.4                                       L96           4-CF.sub.3C.sub.6 H.sub.4                                       L97           2-FC.sub.6 H.sub.4                                              L98           3-FC.sub.6 H.sub.4                                              L99           4-FC.sub.6 H.sub.4                                              L100          2-ClC.sub.6 H.sub.4                                             L101          3-ClC.sub.6 H.sub.4                                             L102          4-ClC.sub.6 H.sub.4                                             L103          2-BrC.sub.6 H.sub.4                                             L104          3-BrC.sub.6 H.sub.4                                             L105          4-BrC.sub.6 H.sub.4                                             L106          2,3-F.sub.2C.sub.6 H.sub.3                                      L107          2,4-F.sub.2C.sub.6 H.sub.3                                      L108          2,5-F.sub.2C.sub. 6 H.sub.3                                     L109          2,6-F.sub.2C.sub.6 H.sub.3                                      L110          2,3-Cl.sub.2C.sub.6 H.sub.3                                     L111          2,4-Cl.sub.2C.sub.6 H.sub.3                                     L112          2,5-Cl.sub.2C.sub.6 H.sub.3                                     L113          2,6-Cl.sub.2C.sub.6 H.sub.3                                     L114          3,4-Cl.sub.2C.sub.6 H.sub.3                                     L115          3,5-Cl.sub.2C.sub.6 H.sub.3                                     L116          2,3,4-Cl.sub.3C.sub.6 H.sub.2                                   L117          2,3,5-Cl.sub.3C.sub.6 H.sub.2                                   L118          2,4,6-Cl.sub.3C.sub.6 H.sub.2                                   L119          3,4,5-Cl.sub.3C.sub.6 H.sub.2                                   L120          2-CNC.sub.6 H.sub.4                                             L121          3-CNC.sub.6 H.sub.4                                             L122          4-CNC.sub.6 H.sub.4                                             L123          2-OCH.sub.3C.sub.6 H.sub.4                                      L124          3-OCH.sub.3C.sub.6 H.sub.4                                      L125          4-OCH.sub.3C.sub.6 H.sub.4                                      L126          2-OC.sub.2 H.sub.5C.sub.6 H.sub.4                               L127          3-OC.sub.2 H.sub.5C.sub.6 H.sub.4                               L128          4-OC.sub.2 H.sub.5C.sub.6 H.sub.4                               L129          2-O-n-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L130          3-O-n-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L131          4-O-n-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L132          2-O-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L133          3-O-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L134          4-O-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L135          2,3-(OCH.sub.3).sub.2C.sub.6 H.sub.3                            L136          2,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3                            L137          2,5-(OCH.sub.3).sub.2C.sub.6 H.sub.3                            L138          2,6-(OCH.sub.3).sub.2C.sub.6 H.sub.3                            L139          3,4-(OCH.sub.3).sub.2C.sub.6 H.sub.3                            L140          3,5-(OCH.sub.3).sub.2C.sub.6 H.sub.3                            L141          3,4,5-(OCH.sub.3).sub.3C.sub.6 H.sub.2                          L142          2-OCF.sub.3C.sub.6 H.sub.4                                      L143          3-OCF.sub.3C.sub.6 H.sub.4                                      L144          4-OCF.sub.3C.sub.6 H.sub.4                                      L145          2-OCF.sub.2 CHF.sub.2C.sub.6 H.sub.4                            L146          3-OCF.sub.2 CHF.sub.2C.sub.6 H.sub.4                            L147          4-OCF.sub.2 CHF.sub.2C.sub.6 H.sub.4                            L148          2-SCH.sub.3C.sub.6 H.sub.4                                      L149          3-SCH.sub.3C.sub.6 H.sub.4                                      L150          4-SCH.sub.3C.sub.6 H.sub.4                                      L151          2-SC.sub.2 H.sub.5C.sub.6 H.sub.4                               L152          3-SC.sub.2 H.sub.5C.sub.6 H.sub.4                               L153          4-SC.sub.2 H.sub.5C.sub.6 H.sub.4                               L154          2-S-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L155          3-S-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L156          4-S-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                            L157          2,4-(SCH.sub.3).sub.2C.sub.6 H.sub.3                            L158          2-SCF.sub.3C.sub.6 H.sub.4                                      L159          3-SCF.sub.3C.sub.6 H.sub.4                                      L160          4-SCF.sub.3C.sub.6 H.sub.4                                      L161          2-NO.sub.2C.sub.6 H.sub.4                                       L162          3-NO.sub.2C.sub.6 H.sub.4                                       L163          4-NO.sub.2C.sub.6 H.sub.4                                       L164          2,3-(NO.sub.2).sub.2C.sub.6 H.sub.3                             L165          2,4-(NO.sub.2).sub.2C.sub.6 H.sub.3                             L166          2,5-(NO.sub.2).sub.2C.sub.6 H.sub.3                             L167          2,6-(NO.sub.2).sub.2C.sub.6 H.sub.3                             L168          3,4-(NO.sub.2).sub.2C.sub.6 H.sub.3                             L169          3,5-(NO.sub.2).sub.2C.sub.6 H.sub.3                             L170          2-CHOC.sub.6 H.sub.4                                            L171          3-CHOC.sub.6 H.sub.4                                            L172          4-CHOC.sub.6 H.sub.4                                            L173                                                                                         ##STR70##                                                      L174                                                                                         ##STR71##                                                      L175                                                                                         ##STR72##                                                      L176                                                                                         ##STR73##                                                      L177                                                                                         ##STR74##                                                      L178                                                                                         ##STR75##                                                      L179                                                                                         ##STR76##                                                      L180                                                                                         ##STR77##                                                      L181                                                                                         ##STR78##                                                      L182                                                                                         ##STR79##                                                      L183                                                                                         ##STR80##                                                      L184                                                                                         ##STR81##                                                      L185          1-naphthyl                                                      L186          2-naphthyl                                                      L187          C.sub.6 H.sub.5                                                 L188          piperidino                                                      L189          tetrahydrofur-3-yl                                              L190          thiazol-2-yl                                                    L191          5-methyl-thiazol-2-yl                                           L192          5-ethyl-thiazol-2-yl                                            L193          5-n-propyl-thiazol-2-yl                                         L194          4-methyl-5-carboxy-thiazol-2-yl                                 L195          cyclopropylmethyl                                               ______________________________________                                    

The compounds Ia, or the herbicidal agents containing them, may beapplied for instance in the form of directly sprayable solutions,powders, suspension (including high-percentage aqueous, oily or othersuspensions), dispersions, emulsions, oil dispersions, pastes, dusts,broadcasting agents, or granules by spraying, atomizing, dusting,broadcasting or watering. The forms of application depend entirely onthe purpose for which the agents are being used, but they must ensure asfine a distribution of the active ingredients according to the inventionas possible.

For the preparation of solutions, emulsions, pastes and oil dispersionsto be sprayed direct, mineral oil fractions of medium to high boilingpoint, such as kerosene or diesel oil, further coal-tar oils, and oilsof vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons such as benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives suchas methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,etc., and strongly polar solvents such as dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes,dispersions, wettable powders or water-dispersible granules by addingwater. To prepare emulsions, pastes and oil dispersions the ingredientsas such or dissolved in an oil or solvent may be homogenized in water bymeans of wetting or dispersing agents, adherents or emulsifiers.Concentrates which are suitable for dilution with water may be preparedfrom active ingredient, wetting agent, adherent, emulsifying ordispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of ligninsulfonic acid, naphthalenesulfonic acids,phenolsulfonic acid, alkylaryl sulfonates, alkyl sulfates, and alkylsulfonates, alkali metal and alkaline earth metal salts ofdibutylnatphthalenesulfonic acid, lauryl ether sulfate, fatty alcoholsulfates, alkali metal and alkaline earth metal salts or fatty acids,salts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsor sulfated fatty alcohol glycol ethers, condensation products ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensation products of naphthalene or naphthalene ornaphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneoctylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenoland ethoxylated nonylphenol, alkylphenol polyglycol etherstributylphenyl polyglycol ethers, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylatedpolyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitolesters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dust and broadcasting agents may be prepared by mixing orgrinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silicic acid, silica gels,silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole,loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesiumsulfate, magnesium oxide, ground plastics, fertilizers such as ammoniumsulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetableproducts such as grain flours, bark meal, wood meal, and nutshell meal,cellulosic powders, etc.

Examples of such formulations are as follows:

I. 90 parts by weight of compound no. 1006 is mixed with 10 parts byweight of N-methyl-alpha-pyrrolidone. A mixture is obtained which issuitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 1006 is dissolved in a mixtureconsisting of 80 parts by weight of xylene, 10 parts by weight of theadduct of 8 to 10 moles of ethylene oxide and 1 mole of oleicacid-N-monoethanolamide, 5 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40moles of ethylene oxide and 1 mole of castor oil. By pouring thesolution into water and uniformly distributing it therein, an aqueousdispersion is obtained.

III. 20 parts by weight of compound no. 1002 is dissolved in a mixtureconsisting of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 7 moles of ethyleneoxide and 1 mole of isooctylphenol, and 10 parts by weight of the adductof 40 moles of ethylene oxide and 1 mole of castor oil. By pouring thesolution into 1000,000 parts by weight of water and finely distributingit therein, an aqueous dispersion is obtained containing 0.02% by weightof the active ingredient.

IV. 20 parts by weight of compound no. 1049 is dissolved in a mixtureconsisting of 25 parts by weight of cyclohexanol, 65 parts by weight ofa mineral oil fraction having a boiling point between 210° and 280° C.,and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1mole of castor oil. By pouring the solution into 100,000 parts by weightof water and uniformly distributing it therein, an aqueous dispersion isobtained containing 0.02% by weight of the active ingredient.

V. 20 parts by weight of compound no. 3038 is well mixed with 3 parts byweight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid,17 parts by weight of the sodium salt of a lignin-sulfonic acid obtainedfrom a sulfite waste liquor, and 60 parts by weight of powdered silicagel, and triturated in a hammer mill. By uniformly distributing themixture in 20,000 parts by weight of water, a spray liquor is obtainedcontaining 0.1% by weight of the active ingredient.

VI. 3 parts by weight of compound no. 1075 is intimately mixed with 97parts by weight of particulate kaolin. A dust is obtained containing 3%by weight of the active ingredient.

VII. 30 parts by weight of compound no. 1220 is intimately mixed with amixture consisting of 92 parts by weight of powdered silica gel and 8parts by weight of paraffin oil which has been sprayed onto the surfaceof this silica gel. A formulation of the active ingredient is obtainedhaving good adherence.

VIII. 20 parts of compound no. 1026 is intimately mixed with 2 parts ofthe calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fattyalcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate and 68 parts of a paraffinic mineraloil. A stable oily dispersion is obtained.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % byweight of active ingredient.

The active ingredient may be applied pre- or (preferably) postemergence.If certain crop plants tolerate the active ingredients less well,application techniques may be used in which the herbicidal agents aresprayed from suitable equipment in such a manner that the leaves ofsensitive crop plants are if possible not touched, and the agents reachthe soil or the unwanted plants growing beneath the crop plants(post-directed, lay-by treatment).

The application rates depend on the objective to be achieved, the timeof the year, the plants to be combated and their growth stage, and arefrom 0.001 to 5.0, preferably 0.0 to 1.0, kg of active ingredient perhectare.

In view of the spectrum of unwanted plants which can be combated, thetolerance of the novel compounds by crop plants, and in view of thenumber of application methods possible, the compounds of the formula Ia,or agents containing them, may be used in a further large number ofcrops for removing unwanted plants. The following crops are given by wayof example:

    ______________________________________                                        Botanical name       Common name                                              ______________________________________                                        Allium cepa          onions                                                   Ananas comosus       pineapples                                               Arachis hypogaea     peanuts (groundnuts)                                     Asparagus officinalis                                                                              asparagus                                                Avena sativa         oats                                                     Beta vulgaris spp. altissima                                                                       sugarbeets                                               Beta vulgaris spp. rapa                                                                            fodder beets                                             Beta vulgaris spp. esculenta                                                                       table beets, red beets                                   Brassica napus var. napus                                                                          rapeseed                                                 Brassica napus var. napobrassica                                                                   swedes                                                   Brassica napus var. rapa                                                                           turnips                                                  Brassica rapa var. silvestris                                                 Camellia sinensis    tea plants                                               Carthamus tinctorius safflower                                                Carya illinoinensis  pecan trees                                              Citrus limon         lemons                                                   Citrus maxima        grapefruits                                              Citrus reticulata    mandarins                                                Citrus sinensis      orange trees                                             Coffea arabica (Coffea canephora,                                                                  coffee plants                                            Coffea liberica)                                                              Cucumis melo         melons                                                   Cucumis sativus      cucumbers                                                Cynodon dactylon     Bermudagrass                                             Elais guineensis     oil palms                                                Fragaria vesca       strawberries                                             Glycine max          soybeans                                                 Gossypium hirsutum (Gossypium                                                                      cotton                                                   arboreum, Gossypium herbaceum,                                                Gossypium vitifolium)                                                         Helianthus annuus    sunflowers                                               Helianthus tuberosus Jerusalem artichoke                                      Hevea brasiliensis   rubber plants                                            Hordeum vulgare      barley                                                   Humulus lupulus      hops                                                     Ipomoea batatas      sweet potatoes                                           Juglans regia        walnut trees                                             Lactuca sativa       lettuce                                                  Lens culinaris       lentils                                                  Linum usitatissimum  flax                                                     Lycopersicon lycopersicum                                                                          tomatoes                                                 Malus spp.           apple trees                                              Manihot esculenta    cassava                                                  Medicago sativa      alfalfa (lucerne)                                        Mentha piperita      peppermint                                               Musa spp.            banana plants                                            Nicotiana tabacum (N. rustica)                                                                     tobacco                                                  Olea europaea        olive trees                                              Oryza sativa         rice                                                     Panicum miliaceum    millet                                                   Phaseolus lunatus    limabeans                                                Phaseolus mungo      mungbeans                                                Phaseolus vulgaris   snapbeans, green beans,                                                       dry beans                                                Pennisetum glaucum   pearl millet                                             Petroselinum crispum spp. tuberosum                                                                parsley                                                  Picea abies          Norway spruce                                            Abies alba           fir trees                                                Pinus spp.           pine trees                                               Pisum sativum        English peas                                             Prunus avium         cherry trees                                             Prunus domestica     plum trees                                               Prunus dulcis        almond trees                                             Prunus persica       peach trees                                              Pyrus communis       pear trees                                               Ribes sylvestre      redcurrants                                              Ribes uva-crispa     gooseberries                                             Ricinus communis     castor-oil plants                                        Saccharum officinarum                                                                              sugar cane                                               Secale cereale       rye                                                      Sesamum indicum      sesame                                                   Solanum tuberosum    Irish potatoes                                           Sorghum bicolor (s. vulgare)                                                                       sorghum                                                  Sorghum dochna       sorgo                                                    Spinacia oleracea    spinach                                                  Theobroma cacao      cacao plants                                             Trifolium pratense   red clover                                               Triticum aestivum    wheat                                                    Triticum durum       durum wheat                                              Vaccinium corymbosum blueberries                                              Vaccinium vitis-idaea                                                                              cranberries                                              Vicia faba           tick beans                                               Vigna sinensis (V. unguiculata)                                                                    cow peas                                                 Vitis vinifera       grapes                                                   Zea mays             Indian corn, sweet corn,                                                      maize                                                    ______________________________________                                    

To increase the spectrum of action and to achieve synergistic effects,the isoxazole-(isothiazole)-5-carboxamides of the formula Ia may bemixed and applied together with numerous representatives of otherherbicidal or growth-regulating active ingredient groups. Examples ofsuitable components are diazines, 4H-3,1-benzoxazine derivatives,benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates,thiolcarbamates, halocarboxylic acids, trazines, amides, ureas, diphenylethers, triazinones, uracils, benzofuran derivatives,cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids,sulfonylureas, imidazolinones, (hetero)aryloxyphenylpropionic acids andsalts, esters and amides thereof, etc.

It may also be useful to apply the compounds of the formula Ia, eitheralone or in combination with other herbicides, in admixture with othercrop protection agents, e.g., agents for combating pests orphytopathogenic fungi or bacteria. The compounds may also be mixed withsolutions of mineral salts used to remedy nutritional or trace elementdeficiencies. Non-phytotoxic oils and oil concentrates may also beadded.

USE EXAMPLES

The action of the isoxazole-(isothiazole)-5-carboxamides of the formulaIa on plant growth is demonstrated in greenhouse experiments.

The vessels employed were plastic flowerpots having a volume of 300 cm³and filled with a sandy loam containing about 3.0% humus. The seeds ofthe test plants were sown separately, according to species.

For the preemergence treatment, the formulated active ingredients wereapplied to the surface of the soil immediately after the seeds had beensown. The compounds were emulsified or suspended in water as vehicle,and sprayed through finely distributing nozzles. The application ratewas 0.5 kg of active ingredient per hectare. After the agents had beenapplied, the vessels were lightly sprinkler-irrigated to inducegermination and growth. Transparent plastic covers were then placed onthe vessels until the plants had taken root. The cover ensure uniformgermination of the plants, insofar as this was not impaired by theactive ingredients.

For postemergence treatment, either plants which had been sown in thepots and grown there were selected, or they were cultivated separatelyas seedlings and transplanted to the pots a few days before beingtreated.

The plants were grown, depending on growth form, to a height of 3 to 15cm before being treated with the active ingredients, which weresuspended or emulsified in water as vehicle, and sprayed through finelydistributing nozzles. The application rates for postemergence treatmentwere 1.0 and 3.0 kg/ha.

The pots were set up in the greenhouse, species from warmer climates inwarmer areas (20° to 35° C.) and species from moderate climates at 10°to 25° C. The experiments were run for from 2 to 4 weeks. During thistime the plants were tended and their reactions to the varioustreatments assessed. The assessment scale was 0 to 100, 100 denotingnonemergence or complete destruction of at least the visible plantparts, and 0 denoting no damage or normal growth.

The pants used in the greenhouse experiments were Abutilon theophrasti,Centaurea cyanus, Chenopdium album, Chrysanthemum coronarium Echinochloacrus-galli, Gallium aparine, Ipomoea spp., Lolium multiflorum, Menthapiperita, Mercurialis annua, Solanum nigrum, Triticum aestivum, Violaspp. and Zea mays.

Active ingredients no. 1006 selected by way of example combated unwantedplants excellently on preemergence application of 3.0 kg/ha.

For example compounds nos. 1004, 1014, 3018, 1026, 1006, 1049 and 1022had, on postemergence application of 1 to 3 kg/ha, a herbicidal actionon a broad spectrum of unwanted plants. Compounds nos. 1075 and 3038also had a very good herbicidal action on broadleaved plants and weretolerated by Indian corn. Compound no. 1211 had an excellent herbicidalaction and was tolerated by wheat.

We claim:
 1. Isothiazole-5-carboxamides of the formula I ##STR82## whereX is sulfur,R¹ is: hydrogen; C₁ -C₁₀ -alkyl which is unsubstituted orsubstituted by C₁ -C₃ -alkoxy, C₁ -C₃ -haloalkoxy, halogen, cyano orphenyl, which in turn may be substituted by halogen, C₁ -C₄ -alkyl, C₁-C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio,C₁ -C₄ -haloalkylthio, cyano, or nitro; C₁ -C₄ -alkoxy; C₃ -C₈-cycloalkyl which is unsubstituted or substituted by C₁ -C₄ -alkyl orhalogen; phenyl which is unsubstituted or substituted by C₁ -C₆ -alkyl,C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆-alkylthio, C₁ -C₆ -haloalkylthio, halogen, nitro or cyano; or 5- or6-membered heterocyclic radical which is unsubstituted or substituted byC₁ -C₄ -alkyl, carboxyl or C₁ -C₄ -alkoxycarbonyl, said heterocyclicradical being attached via carbon and selected from the group consistingtetrahydrofuryl, tetrahydropyranyl, pyridyl, thienyl, furyl andpyrazolyl; R² is: formyl; 4,5-dihydrooxazol-2-yl; or a radical of theformula --COYR⁵ or --CONR⁶ R⁷,where Y is oxygen or sulfur; R⁵ is:hydrogen; C₁ -C₈ -alkyl which is unsubstituted or substituted by C₁ -C₄-alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy, halogen, cyano, hydroxy,trimethylsily, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄-dialkylamino, C₁ -C₄ -alkylsulfinyl, C₁ -C₄ -alkylsulfonyl, carboxyl,C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -dialkyloaminocarbonyl, C₁ -C₄-dialkoxyphosphonyl, 2-propane-iminooxy, thienyl, furyl,tetrahydrofuryl, phthalimido, pyridyl, benzyloxy, benzoyl which isunsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₃ -alkoxy orhalogen; and phenyl which is unsubstituted or substituted by C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, nitro, cyano,thienyl, furyl tetrohydrofuryl, phthalimido or pyridyl; C₃ -C₈ -alkenylwhich is unsubstituted or substituted by phenyl which in turn may besubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl,halogen, nitro or cyano; C₃ -C₆ -haloalkenyl; C₃ -C₈ -alkynyl which isunsubstituted or substituted by hydroxy or C₁ -C₄ -alkoxy; C₃ -C₆-cycloalkyl; C₅ -C₆ -cycloalkenyl; phenyl which is unsubstituted orsubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl,halogen, nitro, cyano, C₁ -C₄ -alkoxycarbonyl or formylamino; a 5- or6-membered heterocyclic radical selected from the group consisting ofthienyl, furyl, tetrahydrofuryl, triazolyl bonded via nitrogen,imidazolyl bonded via nitrogen, bernzotriazolyl, tetrahydropyranyl,pyridyl, morpholino bonded via nitrogen, or piperidino bonded vianitrogen; C₆ -C₇ -cycloalkanimino; phthalimido; succinimido; or aradical ##STR83## for one equivalent of a cation from the groupconsisting of the alkali metals, alkaline earth metals, manganese,copper, iron, ammonium and substituted ammonium; or a radical ##STR84##where R⁸ and R⁹ independently of one another are C₁ -C₄ -alkyl; C₂ -C₆-alkoxyalkyl; C₃ -C₆ -cycloalkyl; phenyl; furyl; or together form amethylene chain of the formula --(CH₂)_(m) --, where m is from 4 to 7;R⁹ is additionally hydrogen; R⁶ is: hydrogen; C₁ -C₈ -alkyl or C₃ -C₈-cycloalkyl R⁷ is: hydrogen or C₁ -C₈ -alkyl, or R⁶ and R⁷ form amethylene chain having 4 or 5 members; R³ is: hydrogen; C₁ -C₈ -alkylwhich is unsubstituted or substituted by hydroxy, halogen, C₁ -C₄-alkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -dialkylamino; C₃ -C₈ -cycloalkylwhich is unsubstituted or substituted by C₁ -C₄ -alkyl, halogen or C₁-C₄ -haloalkyl; R⁴ is: hydrogen; hydroxyl; C₁ -C₄ -alkoxy; C₁ -C₁₀-alkyl which is unsubstituted or substituted by C₁ -C₄ -alkyloxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -dialkylamino, halogen, C₃ -C₆-cycloalkyl or phenyl, which in turn may be substituted by halogen,cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₁₀-alkenyl or C₃ -C₁₀ -alkynyl which is unsubstituted or substituted byhalogen or C₁ -C₄ -alkoxy; C₃ -C₈ -cycloalkyl which is unsubstituted orsubstituted by C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio, halogen, nitro orcyano; C₁ -C₄ -dialkylamino; a 3-membered to 6-membered heterocyclicradical which is unsubstituted or substituted by C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl or halogen, said heterocyclic radical being one memberselected from the group consisting of tetrahydropyranyl,tetrahydrofuryl, thiazolyl, pyridyl, pyrimidyl, morpholino bonded vianitrogen and piperidino bonded via nitrogen; phenyl which isunsubstituted or substituted by C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio,halogen, nitro, cyano, formyl, C₁ -C₆ -alkanoyl or C₁ -C₆ -haloalkanoyl;or R³ and R⁴ together from a radical of the structure --(CH₂)_(n)--Y_(p) --(CH₂)_(q) --, where n and q are each 1, 2 or 3, p is 0 or 1and Y is oxygen, sulfur or N-methyl, or the radical of the formula--(CH₂)_(3--CO--;) with the proviso that R³, R⁴, R⁵, R⁶ and R⁷ are notsimultaneously hydrogen; and their agriculturally acceptable salts. 2.Isothiazole-5-carboxamides of the formula I as set forth in claim 1,where R³ is hydrogen.
 3. Isothiazole-5-carboxamides of the formula I asset forth in claim 1, whereR¹ is: hydrogen or C₁ -C₄ -alkyl; R² is:COYR⁵, where Y is oxygen or sulfur and R⁵ is hydrogen, C₁ -C₄ -alkyl,phenyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄-haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, halogen, or the radical##STR85## R³ is hydrogen and R⁴ is C₁ -C₄ -alkyl or C₃ -C₈ -cycloalkyl.4. An isothiazole-5-carboxamide of the formula I as set forth in claim1, where R¹ is n-propyl, R² is propane-2-iminoxycarbonyl, R³ is hydrogenand R⁴ is tert-butyl.
 5. A herbicidal agent comprising an agriculturallyacceptable carrier and an isothiazole-5-carboxamide of the formula I asset forth in claim
 1. 6. A process for combating the growth of unwantedplants wherein said plants and/or the area to be kept free of saidplants are treated with a herbicidally effective amount of anisothiazole-5-carboxamide of the formula I where ##STR86## x is sulfur,R¹ is hydrogen;C₁ -C₁₀ -alkyl which is unsubstituted or substituted byC₁ -C₃ -alkoxy, C₁ -C₃ -haloalkoxy, halogen, cyano or phenyl, which inturn may be substituted by halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁-C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-haloalkylthio, cyano, or nitro; C₁ -C₄ -alkoxy; C₃ -C₈ -cycloalkylwhich is unsubstituted or substituted by C₁ -C₄ -alkyl or halogen;phenyl which is unsubstituted or substituted by C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁-C₆ -haloalkylthio, halogen, nitro or cyano; a 5- or 6-memberedheterocyclic radical which is unsubstituted or substituted by C₁ -C₄-alkyl, carboxyl or C₁ -C₄ -alkoxycarbonyl, said heterocyclic radicalbeing attached via carbon and selected from the group consisting oftetrahydrofuryl, tetrahydropyranyl, pyridyl, thienyl, furyl andpyrazolyl; R² is: formyl; 4,5-dihydrooxazol-2-yl; or a radical of theformula --COYR⁵ or --CONR⁶ R⁷, where Y is oxygen or sulfur; R⁵ is:hydrogen; C₁ -C₈ -alkyl which is unsubstituted or substituted by C₁ -C₄-alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy, halogen, cyano, hydroxy,trimethylsilyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄-dialkylamino, C₁ -C₄ -alkylsulfinyl, C₁ -C₄ -alkylsulfonyl, carboxyl,C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -dialkyloaminocarbonyl, C₁ -C₄-dialkoxyphosphonyl, 2-propane-iminooxy, thienyl, furyl,tetrahydrofuryl, phthalimido, pyridyl, benzyloxy, benzoyl which isunsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₃ -alkoxy orhalogen; and phenyl which is unsubstituted or substituted by C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, nitro, cyano,thienyl, furyl, tetrahydrofuryl phthalimido or pyridyl; C₃ -C₈ -alkenylwhich is unsubstituted or substituted by phenyl which in turn may besubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl,halogen, nitro or cyano; C₃ -C₆ -haloalkenyl; C₃ -C₈ -alkynyl which isunsubstituted or substituted by hydroxy or C₁ -C₄ -alkoxy; C₃ -C₆-cycloalkyl; C₅ -C₆ -cycloalkenyl; phenyl which is unsubstituted orsubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl,halogen, nitro, cyano, C₁ -C₄ -alkoxycarbonyl or formylamino; a 5- or6-membered heterocyclic radical selected from the group consisting ofthienyl, furyl, tetrahydrofuryl, triazolyl bonded via nitrogen,imidazolyl bonded via nitrogen, benzotriazolyl, tetrahydropyranyl,pyridyl, morpholino bonded via nitrogen, or piperidino bonded vianitrogen; C₆ -C₇ -cycloalkanimino; phthalimido; succinimido; or aradical ##STR87## or one equivalent of a cation from the groupconsisting of the alkali metals, alkaline earth metals, manganese,copper, iron, ammonium and substituted ammonium; or a radical ##STR88##where R⁸ and R⁹ independently of one another are C₁ -C₄ -alkyl; C₂ -C₆-alkoxyalkyl; C₃ -C₆ -cycloalkyl; phenyl; furyl; or together form amethylene chain of the formula --(CH₂)_(m) --, where m is from 4 to 7;R⁹ is additionally hydrogen; R⁶ is: hydrogen; C₁ -C₈ -alkyl or C₃ -C₈-cycloalkyl R⁷ is: hydrogen or C₁ -C₈ -alkyl, or R⁶ and R⁷ form amethylene chain having 4 or 5 members; R³ is: hydrogen; C₁ -C₈ -alkylwhich is unsubstituted or substituted by hydroxy, halogen, C₁ -C₄-alkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -dialkylamino; C₃ -C₈ -cycloalkylwhich is unsubstituted or substituted by C₁ -C₄ -alkyl, halogen or C₁-C₄ -haloalkyl; R⁴ is: hydrogen; hydroxyl; C₁ -C₄ -alkoxy; C₁ -C₁₀-alkyl which is unsubstituted or substituted by C₁ -C₄ -alkyloxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -dialkylamino, halogen, C₃ -C₆-cycloalkyl or phenyl, which in turn may be substituted by halogen,cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; C₃ -C₁₀-alkenyl or C₃ -C₁₀ -alkynyl which is unsubstituted or substituted byhalogen or C₁ -C₄ -alkoxy; C₃ -C₈ -cycloalkyl which is unsubstituted orsubstituted by C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio, halogen, nitro orcyano; C₁ -C₄ -dialkylamino; a 3-membered to 6-membered heterocyclicradical which is unsubstituted or substituted by C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl or halogen, said heterocyclic radical being one memberselected from the group consisting of tetrahydropyranyl,tetrahydrofuryl, thiazolyl, pyridyl, pyrimidyl, morpholino bonded vianitrogen and piperidino bonded via nitrogen; phenyl which isunsubstituted or substituted by C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio,halogen, nitro, cyano, formyl, C₁ -C₆ -alkanoyl or C₁ -C₆ -haloalkanoyl,or R³ and R⁴ together form a radical of the structure --(CH₂)_(n)--Y_(p) --(CH₂)_(q) --, where n and q are each 1, 2 or 3, p is 0 or 1and Y is oxygen, sulfur or N-methyl, or the radical of theformula--(CH₂)₃ --CO--; with the proviso that R³, R⁴, R⁵, R⁶ and R⁷ arenot simultaneously hydrogen, and their agriculturally acceptable salts.